Oxalyl chloride → 3-Chloro-6-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)picolinamide

HRID 1469803Notes

Reaction equation

HRID 1469803 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[C:15]([NH2:20])[CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:23][C:24]1[C:25]([C:38](O)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][CH:29]=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:25]([C:38]([NH:20][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[N:13]=[CH:12][N:11]=[C:10]3[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 71680392N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamineHCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acid

Product 1

HCID 716787143-Chloro-6-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)picolinamideYield 43.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-7, 50 mg, 0.164 mmol), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 85 mg, 0.314 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (63 mg, 0.49 mmol) in CH2Cl2 (2 mL) to afford 40 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 11.62 (s, 1H), 10.14 (s, 1H), 8.94 (d, J=7.8 Hz, 1H), 8.77 (s, 1H), 8.32-8.27 (m, 4H), 8.11 (d, J=8.7 Hz, 1H), 7.75-7.64 (m, 2H), 7.51-7.46 (m, 2H), 4.49 (d, J=5.7 Hz, 2H), 1.17 (s, 9H); MS [M+H]+: 557.16.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8d8e84f950d24ddb9c0e7ef08c301774
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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