1-Methylimidazole → 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl)benzamide

HRID 1410025노트

반응식

HRID 1410025 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=O)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[NH:42][C:41](=[O:43])[O:40][N:39]=2)=[CH:34][CH:33]=1.CCN=C=NCCCN(C)C.CN1C=CN=C1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([NH:31][C:32]3[CH:33]=[CH:34][C:35]([C:38]4[NH:42][C:41](=[O:43])[O:40][N:39]=4)=[CH:36][CH:37]=3)=[O:23])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

6

반응물 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 665513433-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acidHCID 1357413233-(4-Aminophenyl)-4,5-dihydro-1,2,4-oxadiazol-5-one hydrochloride

생성물 1

HCID 1362656173-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl)benzamide수율 26.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (40 mg, 0.1 mmol) and 3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one hydrochloride (22 mg, 0.1 mmol) in 3 mL of DCM was added EDCI (58 mg, 0.3 mmol) followed by N-methylimidazole (25 mg, 0.3 mmol). The mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with EtOAc to give 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl)benzamide (15 mg, 26%) as white solid. 1H NMR (300 MHz, DMSO): δ 10.82 (s, 1H), 10.22 (s, 1H), 9.43 (s, 1H), 8.98 (s, 1H), 8.64 (d, 1H, J=8.1 Hz), 8.12-8.02 (m, 3H), 7.87-7.54 (m, 5H), 7.01 (d, 1H, J=9.0 Hz), 3.82 (s, 3H), 3.76 (s, 3H). LC-MS: 568 [M+H]+, tR=1.54 min. HPLC: 97.16% at 214 nm, 96.94% at 254 nm, tR=2.86 min.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel eluting with EtOAc

출처 및 근거

ORD 기록
ord-57510a5a53e445ec8da8b2421982c36a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921383B2

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