Trifluoroacetic acid → [6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yl]-piperidin-4-yl-amine

HRID 448565Notes

Reaction equation

HRID 448565 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([N:21]3[C:29]4[C:24](=[CH:25][C:26]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:27][CH:28]=4)[CH2:23][CH2:22]3)[N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:33][S:30]([C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[N:21]([C:19]1[N:18]=[CH:17][N:16]=[C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:20]=1)[CH2:22][CH2:23]2)(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 580741254-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66894566[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yl]-piperidin-4-yl-amineYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 6b obtained above was diluted with 5 mL of DCM and trifluoroacetic acid (5 mL, 60 eq) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated under a stream of nitrogen overnight and purified on preparative HPLC to afford 104 mg (17%) of 6c.

Workup

  1. additionwas added
  2. concentrationthen concentrated under a stream of nitrogen overnight
  3. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-ecbd6cef39034ec8811f4a4b7a3e07b0
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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