Water → 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine

HRID 1773325노트

반응식

HRID 1773325 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:20](=[O:21])[C:19]2[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17](Br)=[N:16][C:15]=2[N:14]([CH3:27])[C:12]1=[O:13].[C:28]([O:32][C:33]([C@@H:35]1[CH2:40][CH2:39][CH2:38][N:37](N)[CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].O.C[N:50](C)C=O>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:20](=[O:21])[C:19]2[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:37]3[CH2:38][CH2:39][CH2:40][CH:35]([C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[C@@H:36]3[NH2:50])=[N:16][C:15]=2[N:14]([CH3:27])[C:12]1=[O:13]

참가 물질

6

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 29939704(R)-3-tert-butoxycarbonyl-aminopiperidineHCID 1180349991-[(1,3-Benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

생성물 1

HCID 1180349821-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine수율 90.8%

실험 절차

By utilizing the well known method, 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 2b (400 mg, 0.9 mmol) was dissolved in N,N-dimethylformamide (6 ml). (R)-3-tert-butoxycarbonyl-aminopiperidine (180 mg, 0.9 mmol) and potassium carbonate (186.5 mg, 1.35 mmol) were added to give a reaction mixture. The reaction mixture was reacted at 75° C. for 2 hours, and TLC was used to monitor the reaction progress. After the reaction was completed, the obtained reaction mixture was cooled to room temperature. The cooled reaction solution was poured into water, suction filtered, and the obtained solid was washed with water, dried to give 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine 2c (460 mg, yellow solid), yield: 90.8%.

후처리

  1. customto give a reaction mixture
  2. customThe reaction mixture was reacted at 75° C. for 2 hours
  3. customthe obtained reaction mixture
  4. customThe cooled reaction solution
  5. filtrationfiltered
  6. washthe obtained solid was washed with water
  7. customdried

출처 및 근거

ORD 기록
ord-5a99a8d93b1d4c02a41ce791b829802b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255098B2

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