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 1773325Notes

Reaction equation

HRID 1773325 reaction equation
[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]

Participants

6

Reactant 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

Product 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]-xanthineYield 90.8%

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-5a99a8d93b1d4c02a41ce791b829802b
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

Loading…