Oxalyl chloride → HCID 71678718, compound

HRID 1469810Notes

Reaction equation

HRID 1469810 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]([O: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)[CH2:4][CH2:3]1.[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:27][C:23]=1[C:24](O)=[O:25].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])=[CH:27][C:23]=1[C:24]([NH:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[O:8][CH:5]1[CH2:4][CH2:3][C:2]([CH3:20])([CH3:1])[CH2:7][CH2:6]1)=[O:25]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 86692278HCID 86692278, compound

Product 1

HCID 71678718HCID 71678718, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-((4,4-dimethylcyclohexyl)oxy)quinazolin-8-amine (Intermediate-10, 50 mg, 0.185 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 99 mg, 0.369 mmol), oxalyl chloride (70 mg, 0.55 mmol), DMF (1 drop) and DIPEA (72 mg, 0.56 mmol) in CH2Cl2 (3 mL) to afford 50 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.24 (s, 1H), 8.80 (s, 2H), 8.18 (m, 1H), 7.90 (d, J=7.2 Hz, 1H), 7.73-7.71 (m, 1H), 7.59-7.54 (m, 2H), 7.39 (d, J=7.8 Hz, 1H), 5.38 (m, 1H), 4.30 (d, J=6.0 Hz, 2H), 1.95 (m, 2H), 1.81 (m, 2H), 1.51 (m, 2H), 1.34 (m, 2H), 1.12 (s, 9H), 1.00 (s, 3H), 0.97 (s, 3H); MS (m/z): 523.07 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-2919caa30eab434f937834041a583aa0
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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