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

HRID 1469804노트

반응식

HRID 1469804 반응식
[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: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: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: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

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 716803914-(3-(Trifluoromethyl)phenoxy)quinazolin-8-amineHCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acid

생성물 1

HCID 866922753-Chloro-6-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinazolin-8-yl)picolinamide수율 52.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared following the procedure described in Example-1 using 4-(3-(trifluoromethyl)phenoxy)quinazolin-8-amine (Intermediate-8, 50 mg, 0.164 mmol), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 88 mg, 0.326 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (63 mg, 0.49 mmol) in CH2Cl2 (2 mL) to afford 48 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 11.63 (s, 1H), 9.06 (d, J=7.8 Hz, 1H), 8.86 (s, 1H), 8.33 (br t, 1H), 8.12 (d, J=8.1 Hz, 2H), 7.88-7.82 (m, 2H), 7.76 (m, 3H), 7.48 (d, J=8.4 Hz, 1H), 4.48 (d, J=5.4 Hz, 2H), 1.16 (s, 9H); MS [M+H]+: 558.11.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-355b7e6179f746f4a6483b2585a51e87
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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