Oxalyl chloride → HCID 71679055, compound

HRID 1469820Notes

Reaction equation

HRID 1469820 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH2:19])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[Cl:24][C:25]1[C:30]([C:31](O)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:27][CH:26]=1.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[C:30]([C:31]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[CH:11][N:10]=[C:9]3[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:20]([F:21])([F:23])[F:22])[CH:4]=2)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692285HCID 86692285, compound

Product 1

HCID 71679055HCID 71679055, compoundYield 8.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(4-fluoro-3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-17, 100 mg, 0.31 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 178 mg, 0.62 mmol), oxalyl chloride (118 mg, 0.93 mmol), DMF (1 drop) and DIPEA (120 mg, 0.93 mmol) in CH2Cl2 (5 mL) to afford 16 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.62 (s, 1H), 10.15 (s, 1H), 8.82-8.79 (d, J=8.1 Hz, 1H), 8.69 (s, 1H), 8.33-8.30 (m, 3H), 8.16 (br t, 1H), 7.75-7.69 (t, J=8.4 Hz, 1H), 7.62-7.55 (d, J=10.2 Hz, 1H), 7.42-7.34 (m, 2H), 4.32-4.30 (d, J=5.4 Hz, 2H), 1.14 (s, 9H); MS (m/z): 592.28 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d24c68f3a6694001acba61fbc38ffb44
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…