Oxalyl chloride → HCID 71679714, compound

HRID 1469843Notes

Reaction equation

HRID 1469843 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([CH3:16])[N:6]=1)([CH3:3])[CH3:2].[Cl:17][C:18]1[C:23]([C:24](O)=[O:25])=[C:22]([F:27])[C:21]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:20][CH:19]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:17][C:18]1[C:23]([C:24]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]=[C:7]([CH3:16])[N:6]=[C:5]3[NH:4][CH:1]([CH3:3])[CH3:2])=[O:25])=[C:22]([F:27])[C:21]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692297HCID 86692297, compound

Product 1

HCID 71679714HCID 71679714, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-isopropyl-2-methylquinazoline-4,8-diamine (Intermediate-50, 30 mg, 0.14 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 60 mg, 0.20 mmol), oxalyl chloride (38 mg, 0.30 mmol), DMF (1 drop) and DIPEA (77 mg, 0.60 mmol) in CH2Cl2 (2 mL) to afford 23 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.16 (s, 1H), 8.65 (d, J=7.6 Hz, 1H), 8.12-8.01 (t, J=8.4 Hz, 1H), 7.92 (d, J=7.6 Hz, 1H), 7.43 (d, J=7.7 Hz, 1H), 7.41-7.35 (m, 3H), 4.57-4.52 (m, 1H), 4.30 (d, J=5.6 Hz, 2H), 2.44 (s, 3H), 1.25 (s, 3H), 1.24 (s, 3H), 1.13 (s, 9H); MS (m/z): 486.27 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e3b866852b6e44a6bd723c408b28cc28
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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