Trifluoroacetic acid → HCID 86716116, compound

HRID 627554Notes

Reaction equation

HRID 627554 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][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)[CH:8]=2)[N:3]=1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>>[Cl:1][C:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([CH:33]3[CH2:38][CH2:37][CH2:36][NH:35][CH2:34]3)([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[OH:39])[CH:8]=2)[N:3]=1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86716118HCID 86716118, compound

Product 1

HCID 86716116HCID 86716116, compound

Procedure

tert-Butyl 3-((2,4-dichloro-3-phenylquinolin-6-yl)(hydroxy)(pyridin-3-yl)methyl)piperidine-1-carboxylate (88 mg, 0.11 mmol, Example 5) was treated with TFA (0.8 mL) at room temperature for 1 hour and concentrated to give the title compound. 1H NMR (400 MHz, MeOH-d4) δ 9.05 (s, 1H), 8.56-8.72 (m, 3H), 8.02-8.09 (m, 2H), 7.91 (dd, J=5.56, 8.08 Hz, 1H), 7.49-7.58 (m, 2H), 7.29-7.37 (m, 2H), 7.10-7.22 (m, 1H), 3.37-3.46 (m, 1H), 3.27-3.34 (m, 1H), 3.11 (d, J=11.12 Hz, 1H), 3.01 (d, J=12.13 Hz, 1H), 2.84-2.98 (m, 1H), 1.96-2.08 (m, 1H), 1.78-1.96 (m, 1H), 1.64-1.74 (m, 2H); MS m/e 464.4 [M+H]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-45fc18f915ed409987e017a1da0a0cb2
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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