Acetone → Acetoacetic Acid

HRID 17159

반응식

HRID 17159 반응식
[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]

참가 물질

5

반응물 2

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

생성물 2

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-367b7d43e9bc41959719091afb7378aa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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