Ammonia → HCID 86592035, compound

HRID 1349550Notes

Reaction equation

HRID 1349550 reaction equation
COC(=O)C.C[O:7][C:8](=O)[CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[C@@H:16]([CH3:30])[CH2:15][C@H:14]2[N:31]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:32](=[O:35])[CH2:33][CH3:34].[NH3:44]>CO>[C:8]([CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21](=[O:29])[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)[C@@H:16]([CH3:30])[CH2:15][C@H:14]2[N:31]([C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)[C:32](=[O:35])[CH2:33][CH3:34])(=[O:7])[NH2:44]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6584Methyl AcetateHCID 86592034HCID 86592034, compound

Product 1

HCID 86592035HCID 86592035, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-Cis-N-[6-carbamoylmethoxy-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-propionamide was prepared from (±)-cis-4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-acetic acid methyl ester. To solid (±)-cis-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-acetic acid methyl ester (76 mg, 0.14 mmol) was added a solution of ammonia in methanol (2 M, 10 mL). The resulting solution was stirred over night at room temperature and concentrated. The resulting crude amide was purified by silica gel chromatography (100% hexanes—100% ethyl acetate gradient) to afford pure product (59 mg, 76%).

Workup

  1. concentrationconcentrated
  2. customThe resulting crude amide was purified by silica gel chromatography (100% hexanes—100% ethyl acetate gradient)

Sources & evidence

ORD record
ord-288f5a3799714c4f8d574fef35d786e6
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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