Ammonia → HCID 86592035, compound

HRID 1785901Notes

Reaction equation

HRID 1785901 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C@@H:11]([CH3:25])[CH2:10][C@H:9]2[N:26]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:27](=[O:30])[CH2:28][CH3:29].[NH3:39]>CO>[C:3]([CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16](=[O:24])[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C@@H:11]([CH3:25])[CH2:10][C@H:9]2[N:26]([C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C:27](=[O:30])[CH2:28][CH3:29])(=[O:2])[NH2:39]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 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 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-c7dd50cda3cc4df084e203a5b26f899c
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…