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

HRID 1469804ノート

反応式

HRID 1469804 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-355b7e6179f746f4a6483b2585a51e87
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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