HCID 57752815, compound → HCID 69061708, compound

HRID 225452Notes

Reaction equation

HRID 225452 reaction equation
[CH:1]1([O:6][C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH:15]3[C:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[CH:19]=[C:18]([CH:26]([NH2:33])[C:27]4[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=4)[C:17]4[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:16]3=4)[CH2:11][CH2:10]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=C1CCC(=O)N1[O:46][C:47](=O)[O:48][C:49]1([CH:52]2[CH2:54][CH2:53]2)[CH2:51][CH2:50]1>ClCCl.C(N(CC)CC)C>[CH:1]1([O:6][C:7]([N:9]2[CH2:10][CH2:11][N:12]([CH:15]3[C:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[CH:19]=[C:18]([CH:26]([NH:33][C:47]([O:48][C:49]4([CH:52]5[CH2:54][CH2:53]5)[CH2:51][CH2:50]4)=[O:46])[C:27]4[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=4)[C:17]4[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:16]3=4)[CH2:13][CH2:14]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 57752815HCID 57752815, compoundHCID 69064038HCID 69064038, compound

Product 1

HCID 69061708HCID 69061708, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-{6-[Amino-(3-methyl-3H-imidazol-4-yl)-methyl]-8-chloro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl}-piperazine-1-carboxylic acid cyclopentyl ester (60 mg, 0.11 mmol) was dissolved in 5 ml of dichloromethane and 0.2 ml of triethyl amine. Carbonic acid bicyclopropyl-1-yl ester 2,5-dioxo-pyrrolidin-1-yl ester (45 mg, 0.19 mmol) was added and the reaction mixture stirred for 18 hours at ambient temperature under a dry nitrogen atmosphere. The reaction mixture was washed with brine and evaporated to a solid. The solid was chromatographed on silica gel using 5% methanol/dichloromethane as eluent to obtain 49 mg of title product.

Workup

  1. washThe reaction mixture was washed with brine
  2. customevaporated to a solid
  3. customThe solid was chromatographed on silica gel using 5% methanol/dichloromethane as eluent

Sources & evidence

ORD record
ord-c2292915d4eb450da9e519903918d47c
Source dataset
uspto-grants-2009_07
Patent number
US07557107B2

Reaction notes

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