Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-4-fluoro-3-(pivalamidomethyl)benzamide

HRID 1469858Notes

Reaction equation

HRID 1469858 reaction equation
[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH2:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[C:26]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:25]([F:35])[CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:20](=[O:21])[C:19]3[CH:23]=[CH:24][C:25]([F:35])=[C:26]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[C:18]=3[Cl:17])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 866922712-Chloro-4-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

Product 1

HCID 86692307N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-4-fluoro-3-(pivalamidomethyl)benzamideYield 5.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(tert-butyl)quinazoline-4,8-diamine (Intermediate-55, 100 mg, 0.46 mmol), 2-chloro-4-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-64, 159 mg, 0.56 mmol), oxalyl chloride (117 mg, 0.93 mmol), DMF (1 drop) and DIPEA (178 mg, 1.38 mmol) in CH2Cl2 (5 mL) to afford 12 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.05 (s, 1H), 8.71-8.69 (d, J=7.2 Hz, 1H), 8.49 (s, 1H), 8.15-8.13 (d, J=7.8 Hz, 1H), 7.83 (t, 1H), 7.75-7.73 (m, 1H), 7.53-7.47 (m, 2H), 7.40-7.34 (t, J=8.7 Hz, 1H), 4.43 (d, 2H), 1.54 (s, 9H), 1.08 (s, 9H); MS [M+H]+: 486.56.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-06e5ea2abba14952a97e44dfa86559e1
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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