1-Methylimidazole → Methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate

HRID 1410078노트

반응식

HRID 1410078 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]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24](O)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([O:39][CH3:40])=[O:38])=[N:35][CH:36]=1.CN1C=CN=C1.CCN=C=NCCCN(C)C>ClCCl>[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]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([C:37]([O:39][CH3:40])=[O:38])=[N:35][CH:36]=4)=[O:25])[CH2:19]3)[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 12457877Methyl 5-aminopyridine-2-carboxylateHCID 683795141-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid

생성물 1

HCID 66549701Methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate수율 87.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (200 mg, 0.48 mmol) and methyl 5-aminopicolinate (73 mg, 0.48 mmol) in dichloromethane (30 mL) were added the solution of 1-methyl-1H-imidazole (158 mg, 1.92 mmol) and EDCI (368 mg, 1.92 mmol) in dichloromethane (10 mL), the reaction mixture was stirred at room temperature for 15 hours, the solvent was removed in vacuo and methanol (6 mL) was added and stirred for 30 minutes, the solid was collected by filtration and washed with methanol to afford methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate (230 mg, 87.1%) as an orange solid. LC-MS: 550 [M+H]+, tR=1.58 min.

후처리

  1. customthe solvent was removed in vacuo and methanol (6 mL)
  2. additionwas added
  3. stirringstirred for 30 minutes
  4. filtrationthe solid was collected by filtration
  5. washwashed with methanol

출처 및 근거

ORD 기록
ord-57687260d57f42edab20ec1b7ca4edef
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921383B2

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