Oxalyl chloride → HCID 71679880, compound

HRID 1469847Notes

Reaction equation

HRID 1469847 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[C:12]2[C:7](=[C:8]([NH2:13])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1.[Cl:15][C:16]1[C:21]([C:22](O)=[O:23])=[C:20]([F:25])[C:19]([CH2:26][NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:18][CH:17]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:15][C:16]1[C:21]([C:22]([NH:13][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[N:6]=[CH:5][N:4]=[C:3]3[N:2]([CH3:14])[CH3:1])=[O:23])=[C:20]([F:25])[C:19]([CH2:26][NH:27][C:28](=[O:33])[C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 59533987HCID 59533987, compound

Product 1

HCID 71679880HCID 71679880, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4,N4-dimethylquinazoline-4,8-diamine (Intermediate-54, 100 mg, 0.53 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 184 mg, 0.64 mmol), oxalyl chloride (203 mg, 1.6 mmol), DMF (1 drop) and DIPEA (344 mg, 2.67 mmol) in CH2Cl2 (2 mL) to afford 46 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ10.43 (s, 1H), 8.70-8.68 (d, J=7.6 Hz, 1H), 8.50 (s, 1H), 8.14-8.11 (t, J=5.6 Hz, 1H), 7.95-7.93 (d, J=8.4 Hz, 1H), 7.51-7.47 (t, J=8.0 Hz, 1H), 7.41-7.39 (d, J=8.4 Hz, 1H), 7.36-7.32 (t, J=8.0 Hz, 1H), 4.31-4.29 (d, J=5.6 Hz, 2H), 3.35 (s, 3H), 3.31 (s, 3H), 1.13 (s, 9H); MS (m/z): 458.22 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7e3aa3ed00584351b75b21dcb497d64a
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…