Acetyl chloride → HCID 90412008, compound

HRID 1521960Notes

Reaction equation

HRID 1521960 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:21][CH2:20][NH:19][CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:21][CH2:20][N:19]([C:31](=[O:33])[CH3:32])[CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 90412361HCID 90412361, compound

Product 1

HCID 90412008HCID 90412008, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 59F (50 mg, 0.130 mmol) and triethylamine (0.091 mL, 0.651 mmol) in dichloromethane (2 mL) was added acetyl chloride (0.195 mL, 0.195 mmol) at room temperature. The mixture was stirred for 16 hours, concentrated, and purified by reverse phase flash chromatography (silica gel-C18, 15-60% acetonitrile/water/0.1% trifluoroacetic acid) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.95 (d, J=4.1 Hz, 3H), 1.98-2.40 (m, 3H), 3.23-3.42 (m, 2H), 3.45-3.60 (m, 2H), 3.73 (s, 3H), 3.77-3.96 (m, 2H), 6.11 (dd, J=10.4, 1.7 Hz, 1H), 7.08 (dd, J=5.1, 1.6 Hz, 1H), 7.15-7.34 (m, 3H), 8.20 (d, J=5.1 Hz, 1H), 11.81 (s, 1H). MS (ESI+) m/z 354.1 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase flash chromatography (silica gel-C18, 15-60% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6064d79e2b7f43189b0791ce74cb9832
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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