Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-(pivalamidomethyl)benzamide

HRID 1469848Notes

Reaction equation

HRID 1469848 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: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>[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:24](=[O:25])[C:23]3[C:18]([Cl:17])=[CH:19][CH:20]=[C:21]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:32])([CH3:33])[CH3:34])[C:22]=3[F:27])[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 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

Product 1

HCID 71679881N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-(pivalamidomethyl)benzamideYield 13.4%

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), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 146 mg, 0.51 mmol), oxalyl chloride (126 mg, 0.99 mmol), DMF (1 drop) and DIPEA (132 mg, 1.03 mmol) in CH2Cl2 (3 mL) to afford 30 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.39 (s, 1H), 8.69-8.67 (d, J=7.4 Hz, 1H), 8.51 (s, 1H), 8.18-8.16 (m, 2H), 7.54-7.50 (t, J=8.0 Hz, 1H), 7.44-7.40 (m, 2H), 7.37-7.33 (t, J=8.0 Hz, 1H), 4.32-4.30 (d, J=6.0 Hz, 2H), 1.56 (s, 9H), 1.14 (s, 9H); MS (m/z): 486.25 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0682d24788bf4c55a1e24deae7814921
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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