Oxalyl chloride → HCID 71678544, compound

HRID 1469800Notes

Reaction equation

HRID 1469800 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[CH:10]=[CH:9][N:8]=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:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[CH:10]=[CH:9][N:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=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 716780491-(3-(Trifluoromethyl)phenoxy)isoquinolin-5-amine

Product 1

HCID 71678544HCID 71678544, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-amine (Intermediate-6, 70 mg, 0.23 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 129 mg, 0.45 mmol), oxalyl chloride (85 mg, 0.68 mmol), DMF (1 drop) and DIPEA (89 mg, 0.69 mmol) in CH2Cl2 (3 mL) to afford 17 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 11.02 (s, 1H), 8.34 (d, J=8.4 Hz, 1H), 8.21 (br t, 1H), 8.10-8.01 (m, 2H), 7.81-7.67 (m, 6H), 7.47-7.36 (m, 2H), 4.34 (m, 2H), 1.15 (s, 9H); MS [M+H]+: 574.09.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c739bb85fc5e4a488b36f1a79b2758a2
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…