HCID 18378637, compound → HCID 86758696, compound

HRID 2298803Notes

Reaction equation

HRID 2298803 reaction equation
[CH3:1][O:2][CH:3]1[C:11](=[C:12]=[O:13])[C:10]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:9][CH:8]=[C:4]1[C:5]([OH:7])=O.[NH2:25][C:26]1[C:34]2[N:33]=[C:32]([CH3:35])[N:31]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:30]=2[CH:29]=[CH:28][CH:27]=1.OS1C2C=CC=CC=2N=C1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][CH:3]1[C:11](=[C:12]=[O:13])[C:10]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:9][CH:8]=[C:4]1[C:5]([NH:25][C:26]1[C:34]2[N:33]=[C:32]([CH3:35])[N:31]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:30]=2[CH:29]=[CH:28][CH:27]=1)=[O:7]

Participants

6

Reactant 3

HCID 18378637HCID 18378637, compoundHCID 86758697HCID 86758697, compoundHCID 178527226HCID 178527226, compound

Product 1

HCID 86758696HCID 86758696, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)-carbonylbenzoic acid (200 mg), 4-amino-1-tert-butoxycarbonyl-2-methyl-1H-benzimidazole (152 mg), WSCD·HCl [water soluble carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 141 mg] and 1-hydroxybenzotiazole (100 mg) in N,N-dimethylformamide (5 ml) was stirred at room temperature overnight, and the mixture was diluted with ethyl acetate. The solution was washed successively with saturated aqueous sodium hydrogencarbonate solution, water, and brine and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography using chloroform as an eluent to give 2-methoxy-N-[2-methyl-1-(tert-butoxycarbonyl)-1H-benzimidazol-4-yl]-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)-carbonylbenzamide (185 mg).

Workup

  1. washThe solution was washed successively with saturated aqueous sodium hydrogencarbonate solution, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a7a0bb4eff347b29defd26a4f3e34bd
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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