Acetyl chloride → HCID 86716124, compound

HRID 627557Notes

Reaction equation

HRID 627557 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([CH:27]3[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]3)([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[OH:20])[CH:8]=2)[N:3]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].C(Cl)(=O)C.CCN(CC)CC>C(Cl)Cl>[C:33]([N:23]1[CH2:24][CH2:25][CH2:26][CH:21]([C:19]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([Cl:1])[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]3[Cl:18])([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[OH:20])[CH2:22]1)(=[O:34])[CH3:35].[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86716116HCID 86716116, compound

Product 1

HCID 86716124HCID 86716124, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-dichloro-3-phenylquinolin-6-yl)(piperidin-3-yl)pyridin-3-ylmethanol•TFA (19 mg, 0.027 mmol, Example 93), acetyl chloride (10 mg, 0.13 mmol), and Et3N (0.030 mL, 0.22 mmol) in CH2Cl2 (1 mL) was stirred overnight and concentrated. The residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to provide the title compound as a white solid. 1H NMR (400 MHz, MeOH-d4) δ 9.06-9.14 (m, 1H), 8.67-8.77 (m, 3H), 8.02-8.20 (m, 2H), 7.96 (dd, J=5.56, 8.08 Hz, 1H), 7.46-7.58 (m, 3H), 7.30-7.38 (m, 2H), 4.48-4.63 (m, 1H), 3.94 (d, J=13.14 Hz, 0.6H), 3.65 (d, J=9.60 Hz, 0.4H), 2.88-3.16 (m, 2H), 2.45-2.67 (m, 1H), 2.10 (s, 2H), 1.90 (s, 1H), 1.49-1.88 (m, 4H); MS m/e 506.1 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA)

Sources & evidence

ORD record
ord-f3ea4caa90af4029baaeb9c74ac1c939
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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