Oxalyl chloride → 6-Chloro-2-methoxy-3-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinazolin-8-yl)benzamide

HRID 1469836Notes

Reaction equation

HRID 1469836 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[C:16]2[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][N:8]=1.[Cl:23][C:24]1[C:29]([C:30](O)=[O:31])=[C:28]([O:33][CH3:34])[C:27]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:26][CH:25]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:29]([C:30]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[N:10]=[CH:9][N:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)=[O:31])=[C:28]([O:33][CH3:34])[C:27]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 71678385HCID 71678385, compoundHCID 716803914-(3-(Trifluoromethyl)phenoxy)quinazolin-8-amine

Product 1

HCID 716795626-Chloro-2-methoxy-3-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinazolin-8-yl)benzamideYield 32.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-(3-(trifluoromethyl)phenoxy)quinazolin-8-amine (Intermediate-8, 60 mg, 0.19 mmol), 6-chloro-2-methoxy-3-(pivalamidomethyl)benzoic acid (Intermediate-43, 88 mg, 0.29 mmol), oxalyl chloride (55 mg, 0.44 mmol), DMF (1 drop) and DIPEA (74 mg, 0.57 mmol) in CH2Cl2 (2 mL) to afford 36 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.49 (s, 1H), 8.92 (d, J=7.8 Hz, 1H), 8.77 (s, 1H), 8.17-8.11 (m, 2H), 7.86 (m, 2H), 7.74 (m, 3H), 7.30 (m, 2H), 4.29 (d, 2H), 3.84 (s, 3H), 1.15 (s, 9H); MS (m/z): 587.17 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-17faab2e2f004d1fba865894b36425fd
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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