Oxalyl chloride → HCID 71679711, compound

HRID 1469839Notes

Reaction equation

HRID 1469839 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[C:17]3[C:12](=[C:13]([NH2:18])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[Cl:23][C:24]1[C:29]([C:30](O)=[O:31])=[C:28]([F:33])[C:27]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:26][CH:25]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:29]([C:30]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[N:11]=[CH:10][CH:9]=[C:8]3[O:7][C:6]2[CH:19]=[CH:20][C:3]([C:2]([F:1])([F:21])[F:22])=[CH:4][CH:5]=2)=[O:31])=[C:28]([F:33])[C:27]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 71678550HCID 71678550, compound

Product 1

HCID 71679711HCID 71679711, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-(4-(trifluoromethyl)phenoxy)quinolin-8-amine (Intermediate-46, 126 mg, 0.44 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 142 mg, 0.49 mmol), oxalyl chloride (93 mg, 0.74 mmol), DMF (1 drop) and DIPEA (170 mg, 1.32 mmol) in CH2Cl2 (5 mL) to afford 30 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ10.78 (s, 1H), 8.80-8.75 (m, 2H), 8.16 (t, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.90 (d, J=8.4 Hz, 2H), 7.72 (t, J=7.8 Hz, 1H), 7.52 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.4 Hz, 1H), 7.36 (d, J=7.2 Hz, 1H), 6.96 (d, J=5.1 Hz, 1H), 4.31 (d, J=5.4 Hz, 2H), 1.14 (s, 9H); MS (m/z): 574.26 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7d88d3546e0b4b6ea661b14e26532b61
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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