Oxalyl chloride → 6-Chloro-2-fluoro-N-(4-(isopropylamino)quinazolin-8-yl)-3-(pivalamidomethyl)benzamide

HRID 1469850ノート

反応式

HRID 1469850 の反応式
[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]=1

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692303N4-isopropylquinazoline-4,8-diamine

生成物 1

HCID 716798826-Chloro-2-fluoro-N-(4-(isopropylamino)quinazolin-8-yl)-3-(pivalamidomethyl)benzamide収率 12.3%

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 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)+.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-7c21074559974345b6f05b867168b14f
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

読み込み中…