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4-Methylmorpholine → HCID 10305506, compound

HRID 392514
Notes
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Reaction equation

HRID 392514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[C@H:8]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:20]([C:31](O)=[O:32])[CH2:19]3)[C:5]2=[N:6][CH:7]=1.[Na].[N:35]1([CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][NH:43]2)[CH:39]=[CH:38][N:37]=[CH:36]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[C@H:8]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C@@H:20]([C:31]([N:43]4[CH2:44][CH2:45][CH2:46][CH2:47][CH:42]4[CH2:41][CH2:40][N:35]4[CH:39]=[CH:38][N:37]=[CH:36]4)=[O:32])[CH2:19]3)[C:5]2=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226629092-[2-(1H-imidazol-1-yl)ethyl]piperidineHCID 69690116HCID 69690116, compound

Product 1

HCID 10305506
HCID 10305506, compound
Yield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Sodium 1,1-dimethylethyl 4-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(S)-yl)-2(R)-carboxy-1-piperazinecarboxylate (prepared as described in Preparative Example 6 (sodium sat)) (0.1 g, 0.179 mmoles), 2-[2-(1H-imidazol-1-yl)ethyl]piperidine (prepared as described in Preparative Example 57, Step D) (0.0417 g, 0.233 mmoles), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.0446 g, 0.233mmoles), 1-hydroxybenzotriazole (0.0314 g, 0.233 mmoles) and 4-methylmorpholine (0.0512 mL, 0.466 mmoles) were dissolved in anhydrous DMF (4 mL) and the mixture was stirred under argon at 25° C. for 42 h. The solution was evaporated to dryness and the residue was taken up in dichloromethane and washed with 1N NaOH, dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed on silica gel using 2.5%-4.5%-7.5% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (0.0172 g, 14%): HRFABMS: m/z 697.2285 (MH+) (Calcd. m/z 697.2269); δH (CDCl3) 1.38/1.41 (9H, s, CH3), 4.31 (1H, s, H11), 4.68 (1H, bs, H2), 7.03-7.20 (5H, bm, Ar—H and Im-H4 and Im-H5), 7.57 (1H, s, Im-H2), 7.83/8.19 (s, Ar—H) and 8.38 ppm (1H, s, Ar—H2); δC (CDCl3) CH3: 28.4, 28.4, 28.4; CH2: 19.1, 24.8/24.9, 28.3, 30.3, 30.5, 31.4, 40.3, 42.9/43.2, 44.1/44.6, 45.6, 50.2/50.5; CH: 44.1/44.6, 52.4, 78.4, 119.2, 126.2, 127.9, 130.8/130.9, 132.6, 136.7, 141.6, 146.9/147.2; C: 80.4, 119.8/120.2, 134.4, 135.9, 137.0, 141.5, 155.0, 156.7/157.1, 170.3/170.9.

Workup

  1. customThe solution was evaporated to dryness
  2. washwashed with 1N NaOH
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel using 2.5%-4.5%-7.5% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

Sources & evidence

ORD record
ord-91399c74b1c6482985850f0bc6c2ff7c
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800636B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes