Trifluoroacetic acid → (R)-2-[5-Phenylmethylthio-2-(piperidin4-ylamino)-thiazolo[4,5-d]pyrimidin-7-ylamino]-4-methyl-pentan-1-ol

HRID 1831466Notes

Reaction equation

HRID 1831466 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]3[C:22]([NH:23][C@@H:24]([CH2:29][OH:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[N:21][C:20]([S:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[N:19][C:18]=3[N:39]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>ClCCl>[C:33]1([CH2:32][S:31][C:20]2[N:21]=[C:22]([NH:23][C@H:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:29][OH:30])[C:17]3[S:16][C:15]([NH:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[N:39][C:18]=3[N:19]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 86760111(R)-4-[5-Phenylmethylthio-7-(1-hydroxymethyl-3-methyl-butylamino)-thiazolo[4,5-d]pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21035681(R)-2-[5-Phenylmethylthio-2-(piperidin4-ylamino)-thiazolo[4,5-d]pyrimidin-7-ylamino]-4-methyl-pentan-1-olYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (b) (40 mg, 70 μmol) was dissolved in anhydrous dichloromethane (2.5 mL) and trifluoroacetic acid (269 μL, 3.5 mmol) was added. The mixture was stirred at room temperature for two hours. 1M Aqueous potassium carbonate (3.5 mL) followed by 0.1M aqueous sodium hydroxide (1 mL) were added and the product was extracted twice with dichloromethane. The precipitate which formed was filtered off, washed with dichloromethane and dried in vacuo at 40° C. overnight resulting in 24 mg (73% yield) of the title compound as an off-white solid.

Workup

  1. additionwere added
  2. extractionthe product was extracted twice with dichloromethane
  3. customThe precipitate which formed
  4. filtrationwas filtered off
  5. washwashed with dichloromethane
  6. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-f1078afb97e146c6ba7b5210f3973c92
Source dataset
uspto-grants-2006_06
Patent number
US07067657B2

Reaction notes

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