Water → Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate

HRID 1410015노트

반응식

HRID 1410015 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:39]=[CH:38][S:37][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]([C:26]4[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([OH:36])[CH:27]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CI.[C:42]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:39]=[CH:38][S:37][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]([C:26]4[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([O:36][CH3:42])[CH:27]=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 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68379322Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate

생성물 1

HCID 68379417Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate (100 mg, 0.18 mmol) in 2 mL of DMF were added MeI (38 mg, 0.27 mmol) and K2CO3 (37 mg, 0.27 mmol) at room temperature, and then the mixture was stirred for 16 hours. The mixture was poured into water and extracted with EtOAc (3×5 mL). The organic layer was washed with 0.1 N HCl (5 mL) and brine. The organic layer was dried over Na2SO4. After filtration and concentration, the crude methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate was obtained and used the next step without purification (80 mg, 78%). LC-MS: 565 [M+H]+, tR=1.48 min.

후처리

  1. extractionextracted with EtOAc (3×5 mL)
  2. washThe organic layer was washed with 0.1 N HCl (5 mL) and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationAfter filtration and concentration

출처 및 근거

ORD 기록
ord-d7cf4655b95745f6bb76157bdd4fd80b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921383B2

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