Oxalyl chloride → HCID 71679058, compound

HRID 1469822Notes

Reaction equation

HRID 1469822 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:22]2[C:17](=[C:18]([NH2:23])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1.[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:23][C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:17]=2[N:16]=[CH:15][N:14]=[C:13]3[NH:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[F:1])=[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 86692286HCID 86692286, compound

Product 1

HCID 71679058HCID 71679058, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(2-fluoro-4-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-23, 230 mg, 0.71 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 245 mg, 0.85 mmol), oxalyl chloride (161 mg, 1.28 mmol), DMF (1 drop) and DIPEA (275 mg, 2.13 mmol) in CH2Cl2 (8 mL) to afford 70 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.63 (s, 1H), 10.22 (s, 1H), 8.82-8.79 (d, J=8.1 Hz, 1H), 8.59 (s, 1H), 8.28-8.25 (d, J=9.0 Hz, 1H), 8.16 (m, 1H), 7.89-7.83 (m, 2H), 7.75-7.67 (m, 2H), 7.42-7.34 (m, 2H), 4.32-4.30 (d, J=5.4 Hz, 2H), 1.14 (s, 9H); MS (m/z): 592.33 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7b2b3788b27142d4b030d1caa317aac3
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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