Acetone → Acetoacetic Acid

HRID 17159

反応式

HRID 17159 の反応式
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19]C(C)(C)C)=[C:13]([O:25][CH3:26])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:27]=[CH:28]/[CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:4][N:3]=1.[CH3:35][C:36]([CH3:38])=[O:37]>Cl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5](/[CH:27]=[CH:28]/[CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[C:6]=3[S:10][CH:9]=2)=[CH:12][C:13]=1[O:25][CH3:26].[CH3:35][C:36]([CH2:38][C:18]([OH:24])=[O:19])=[O:37]

参加物

5

反応物 2

HCID 180AcetoneHCID 18451456Tert-butyl 4-{4-amino-7-[(1e)-3-(diethylamino)-1-propenyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenylcarbamate

生成物 2

HCID 96Acetoacetic AcidHCID 184507083-(4-Amino-3-methoxyphenyl)-7-[(1e)-3-(diethylamino)-1-propenyl]thieno[3,2-c]pyridin-4-amine

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A mixture of Example 365B (425 mg, 0.88 mmol) in acetone (10 mL) and 6N aqueous hydrochloric acid (2 mL) was stirred for 18 hours at ambient temperature then concentrated under reduced pressure. The residue was then purified by preparative reverse phase HPLC to provide the desired product as the diacetate salt. 1H NMR (DMSO-d6, 400 MHz) δ 7.89 (s, 1H), 7.39 (s, 1H), 6.82 (s, 1H), 6.73 (s, 2H), 6.20 (m, 1H), 5.65 (br s, 2H), 3.78 (s, 3H), 3.30 (d, 2H), 2.56 (q, 4H), 1.88 (s, 6H), 1.01 (t, 6H); MS m/e 383.4 (M+H)+.

後処理

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was then purified by preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-367b7d43e9bc41959719091afb7378aa
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

関連ノート

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