Oxalyl chloride → HCID 71679563, compound

HRID 1469835Notes

Reaction equation

HRID 1469835 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=3[CH:10]=[CH:9][N:8]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[Cl:24][C:25]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:30][C:26]=1[C:27](O)=[O:28].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:24][C:25]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:30][C:26]=1[C:27]([NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[CH:9][N:8]=[C:7]2[O:6][C:5]1[CH:18]=[CH:19][C:2]([F:1])=[C:3]([C:20]([F:23])([F:21])[F:22])[CH:4]=1)=[O:28]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 71678548HCID 71678548, compound

Product 1

HCID 71679563HCID 71679563, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 1-(4-fluoro-3-(trifluoromethyl)phenoxy)isoquinolin-5-amine (Intermediate-42, 80 mg, 0.24 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 134 mg, 0.49 mmol), oxalyl chloride (93 mg, 0.74 mmol), DMF (1 drop) and DIPEA (93 mg, 0.72 mmol) in CH2Cl2 (5 mL) to afford 26 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.75 (s, 1H), 8.30 (d, 1H), 8.21 (t, 1H), 8.08 (d, J=7.5 Hz, 1H), 7.98 (d, J=6.3 Hz, 1H), 7.82-7.55 (m, 7H), 7.37 (d, J=8.4 Hz, 1H), 4.32 (J=5.4 Hz, 2H), 1.14 (s, 9H); MS (m/z): 574.22 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-501c047a3f854ba8a6a18a9d0c6fae97
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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