Thionyl Chloride → 6-Chloro-2-fluoro-3-(isobutyramidomethyl)-N-(4-(isopropylamino)quinazolin-8-yl)benzamide

HRID 1469863ノート

反応式

HRID 1469863 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:33])[CH:30]([CH3:32])[CH3:31])=[CH:19][CH:18]=1.S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>C1COCC1>[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:33])[CH:30]([CH3:31])[CH3:32])=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 866922656-Chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acidHCID 86692303N4-isopropylquinazoline-4,8-diamine

生成物 1

HCID 716802296-Chloro-2-fluoro-3-(isobutyramidomethyl)-N-(4-(isopropylamino)quinazolin-8-yl)benzamide収率 17.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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, 50 mg, 0.25 mmol), 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acid (Intermediate-60, 100 mg, 0.37 mmol), thionyl chloride (1 mL), and DIPEA (127 mg, 0.99 mmol) in THF (2 mL) to afford 20 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.70-8.67 (d, J=7.2 Hz, 1H), 8.48 (s, 1H), 8.37 (t, 1H), 8.11-8.08 (d, J=7.8 Hz, 2H), 7.53 (t, 1H), 7.41 (m, 2H), 4.55 (m, 1H), 4.31 (d, 2H), 2.50 (m, 1H), 1.27 (d, J=6.6 Hz, 6H), 1.05-1.03 (d, J=6.9 Hz, 6H); MS [M+H]+: 458.47.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-6b175323b57c4034b7b2f0872ce9c875
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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