Isopropylamine → HCID 59416781, compound

HRID 1184466Notes

Reaction equation

HRID 1184466 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=2[F:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][CH:25]([NH2:27])[CH3:26].Cl.C(N=C=NCCCN(C)C)C.O.N1(O)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.O>[F:23][C:15]1[CH:16]=[C:17]([C:18](=[O:20])[NH:27][CH:25]([CH3:26])[CH3:24])[CH:21]=[CH:22][C:14]=1[N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1

Participants

8

Reactant 5

HCID 6363IsopropylamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 594168004-(4-(Tert-butoxycarbonyl)piperazin-1-yl)-3-fluorobenzoic acid

Product 1

HCID 59416781HCID 59416781, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-fluorobenzoic acid 302 (1.1 g, 3.39 mmol), propan-2-amine (0.241 g, 4.07 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.975 g, 5.09 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol hydrate (0.779 g, 5.09 mmol) were suspended in DMF (13.57 mL) and 4-methylmorpholine (1.864 mL, 16.96 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 h, diluted with water (50 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (3×50 mL), dried over MgSO4, and concentrated in vacuo to afford the title compound as an off-white solid (1.11 g, 3.04 mmol, 89% yield). ESI-MS: m/z 366 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with brine (3×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a70f944cda8b4d76b4a6f87cc30267f2
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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