Water → 1-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine

HRID 1773323Notes

Reaction equation

HRID 1773323 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17](Br)=[N:16][C:15]=4[N:14]([CH3:27])[C:12]3=[O:13])=[N:7][C:6]=2[CH:28]=1.[C:29]([O:33][C:34]([C@@H:36]1[CH2:41][CH2:40][CH2:39][N:38](N)[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].O.C[N:51](C)C=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:38]5[CH2:39][CH2:40][CH2:41][CH:36]([C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[C@@H:37]5[NH2:51])=[N:16][C:15]=4[N:14]([CH3:27])[C:12]3=[O:13])=[N:7][C:6]=2[CH:28]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 29939704(R)-3-tert-butoxycarbonyl-aminopiperidineHCID 1180352331-[(5-Fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

Product 1

HCID 1180351061-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthineYield 77.6%

Procedure

By utilizing the well known method, 1-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1b (240 mg, 0.51 mmol) was dissolved in N,N-dimethylformamide (5 ml). (R)-3-tert-butoxycarbonyl-aminopiperidine (130 mg, 0.66 mmol) and potassium carbonate (107 mg, 0.78 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 cool water, suction filtered, and the obtained solid was washed with water, dried to give 1-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-tert-butoxycarbonyl-amino-piperidin-1-yl]-xanthine 1c (230 mg, yellow solid), yield: 77.6%.

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. additionwas poured
  6. filtrationfiltered
  7. washthe obtained solid was washed with water
  8. customdried

Sources & evidence

ORD record
ord-e7a2ad883531434fbc484c5995d4cf85
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

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