Acetyl chloride → HCID 86716121, compound

HRID 627556Notes

Reaction equation

HRID 627556 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]([OH:39])([C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[CH:20]3[CH2:25][CH2:24][N:23]([C:26](OC(C)(C)C)=[O:27])[CH2:22][CH2:21]3)[CH:8]=2)[N:3]=1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41].C(Cl)(=O)C.CCN(CC)CC>C(Cl)Cl>[C:26]([N:23]1[CH2:22][CH2:21][CH:20]([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:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[OH:39])[CH2:25][CH2:24]1)(=[O:27])[CH3:40].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 86716123HCID 86716123, compound

Product 1

HCID 86716121HCID 86716121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[(2,4-dichloro-3-phenylquinolin-6-yl)(hydroxy)pyridin-3-ylmethyl]piperidine-1-carboxylate (149 mg, 0.264 mmol, Example 91) was treated with TFA (1 mL) at room temperature for 1 hour and concentrated. A part of the residue (10 mg, 0.027 mmol), 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 9.11 (s, 1H), 8.80 (t, J=7.33 Hz, 1H), 8.70 (d, J=5.56 Hz, 1H), 8.59-8.65 (m, 1H), 8.08-8.15 (m, 1H), 8.01-8.06 (m, 1H), 7.94-8.01 (m, 1H), 7.47-7.57 (m, 3H), 7.33 (t, J=6.57 Hz, 2H), 4.59 (d, J=13.14 Hz, 1H), 3.97 (d, J=13.14 Hz, 1H), 3.10-3.28 (m, 2H), 2.63-2.76 (m, 1H), 1.37-1.67 (m, 4H); MS m/e 506.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-adc22b5fbec1445c938660b6295dcd67
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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