Triethylamine → HCID 178469840, compound

HRID 1258041Notes

Reaction equation

HRID 1258041 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14]([C:16]1[C:17]2[NH:25][CH:24]=[N:23][C:18]=2[CH2:19][CH2:20][NH:21][CH:22]=1)=[O:15])[CH3:12].CCN(CC)CC>C(Cl)Cl>[CH2:11]([O:13][C:14]([C:16]1[C:17]2[NH:25][CH:24]=[N:23][C:18]=2[CH2:19][CH2:20][N:21]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[CH:22]=1)=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 178469762HCID 178469762, compound

Product 1

HCID 178469840HCID 178469840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-fluorobenzoyl chloride was added dropwise to a stirred solution of 3,6,7,8-tetrahydro-imidazo[4,5-d]azepine-4-carboxylic acid ethyl ester (Example 1, 60 mg, 0.29 mmol) and Et3N (0.2 mL) in dry CH2Cl2 at 0° C. under nitrogen. The resulting mixture was allowed to warm to ambient temperature overnight. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel eluting with hexane-EtOAc (80:20) to give the title compound as a yellow solid. 1H-NMR(CDCl3): δ 8.27-8.21 (3H, m), 7.16 (2H, t), 7.00 (1 H, s), 5.10 (1 H, br s), 4.35 (2H, q), 3.56 (2H, m), 3.14 (2H, t), 1.39 (3H, t); MS (ES): 330 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica gel eluting with hexane-EtOAc (80:20)

Sources & evidence

ORD record
ord-2ee61eca8d824bceb8ba50c47c4b6b5a
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

Loading…