Triethylamine → HCID 71547801, compound

HRID 1184553Notes

Reaction equation

HRID 1184553 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][C@@H:8]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)(=[O:13])=[O:12])[CH2:9][C@@H:2]12.C(N(CC)CC)C.[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>ClCCl>[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([N:6]2[CH2:5][CH2:4][N:3]3[CH2:7][C@@H:8]([NH:10][S:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=4)(=[O:13])=[O:12])[CH2:9][C@H:2]3[CH2:1]2)=[O:37])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 71547802HCID 71547802, compound

Product 1

HCID 71547801HCID 71547801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 42 (42 mg, 0.12 mmol) in dichloromethane (5 mL) was added triethylamine (17 mg, 0.168 mmol) followed by 4-fluorobenzoyl chloride (27 mg, 0.168 mmol) in dichloromethane (1 mL). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate, then ethyl acetate/methanol=20:1) to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.20 (m, 1H), 1.80-2.10 (m, 3H), 2.20 (m, 1H), 2.70-2.95 (m, 3H), 3.12 (m, 1H), 3.40-3.70 (m, 2H), 4.45 (m, 1H), 7.22 (m, 2H), 7.42 (m, 2H), 7.82 (m, 1H), 8.05-8.20 (m, 4H); MS (ESI) m/z 472 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-cc81292f351641219b8a382cfa3634d0
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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