4-Methylmorpholine → 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyrid-11-ylidene)-1-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzoyl]piperidine hemihydrate

HRID 1708553Notes

Reaction equation

HRID 1708553 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3CCCCN3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.[CH3:23][C:24]1[N:25]([C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=2)[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][C:27]=2[N:32]=1.O.O[N:44]1[C:48]2C=[CH:50][CH:51]=[CH:52][C:47]=2N=N1.Cl.CN(C)CCCN=C=NCC.C[N:66]1[CH2:71][CH2:70]O[CH2:68][CH2:67]1>ClCCl>[OH2:38].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:52]3[CH2:51][CH2:50][N:44]([C:37](=[O:39])[C:36]4[CH:35]=[CH:34][C:33]([N:25]5[C:26]6[CH:31]=[CH:30][N:29]=[CH:28][C:27]=6[N:32]=[C:24]5[CH3:23])=[CH:41][CH:40]=4)[CH2:48][CH2:47]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:68][CH2:67][N:66]([C:37](=[O:39])[C:36]4[CH:35]=[CH:34][C:33]([N:25]5[C:26]6[CH:31]=[CH:30][N:29]=[CH:28][C:27]=6[N:32]=[C:24]5[CH3:23])=[CH:41][CH:40]=4)[CH2:71][CH2:70]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 104674374-(2-Methyl-1H-imidazo[4,5-C]pyridin-1-YL)benzoic acidHCID 1317187578-chloro-5,6-dihydro-11-H-benzo[5,6]cyclohepta[1,2-b]pyrid-11-ylidene-piperidine

Product 1

HCID 1317187564-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyrid-11-ylidene)-1-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzoyl]piperidine hemihydrateYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(8-chloro-5,6-dihydro-11-H-benzo[5,6]cyclohepta[1,2-b]pyrid-11-ylidene-piperidine (224 mg, 0.75 mmol) and (4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzoic acid (190 mg, 0.75 mmol) in dichloromethane (12 ml) was treated sequentially with 1-hydroxybenzotriazole hydrate (102 mg, 0.75 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (290 mg, 1.5 mmol) and 4-methylmorpholine (165 μl; 1.5 mmol). The mixture was stirred at room temperature for 16 hours, washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 3-4% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (113 mg, 27%) as a colourless foam which was characterised as a hemihydrate. Found: C,71.1; H,5.2; N,12.3. C33H28ClN5O. 0.5 H2O requires C,71.4; H,5.3; N,12.6%.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. customThe residue was purified by chromatography on silica
  5. customevaporated

Sources & evidence

ORD record
ord-e386143fe687420ab3bde02874b5b178
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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