Oxalyl chloride → 6-Chloro-2-fluoro-N-(4-(isopropylamino)quinazolin-8-yl)-3-(pivalamidomethyl)benzamide
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]=[CH:7][N:6]=1)([CH3:3])[CH3:2].[Cl:16][C:17]1[C:22]([C:23](O)=[O:24])=[C:21]([F:26])[C:20]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:19][CH:18]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:16][C:17]1[C:22]([C:23]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][CH:1]([CH3:3])[CH3:2])=[O:24])=[C:21]([F:26])[C:20]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:32])([CH3:31])[CH3:33])=[CH:19][CH:18]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The title compound was prepared following the procedure described in Example-1 using N4-isopropylquinazoline-4,8-diamine (Intermediate-57, 140 mg, 0.69 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 223 mg, 0.78 mmol), oxalyl chloride (147 mg, 1.17 mmol), DMF (1 drop) and DIPEA (267 mg, 2.07 mmol) in CH2Cl2 (5 mL) to afford 40 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.38 (s, 1H), 8.69 (d, J=7.0 Hz, 1H), 8.48 (s, 1H), 8.16-8.14 (t, J=5.8 Hz, 1H), 8.10-8.07 (m, 2H), 7.55-7.51 (t, J=8.0 Hz, 1H), 7.42-7.40 (d, J=8.4 Hz, 1H), 7.36-7.33 (t, J=8.0 Hz, 1H), 4.56-4.51 (m, 1H), 4.31 (d, J=5.8 Hz, 2H), 1.28 (s, 3H), 1.25 (s, 3H), 1.14 (s, 9H); MS (m/z): 472.40 (M+H)+.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-7c21074559974345b6f05b867168b14f
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006257B2
Reaction notes
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