Trifluoroacetic acid → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid pyrrolidin-3-yl ester

HRID 448592Notes

Reaction equation

HRID 448592 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[C:27]([N:29]4[C:37]5[C:32](=[CH:33][C:34]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:36]=5)[CH2:31][CH2:30]4)[N:26]=[CH:25][N:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[C:27]([N:29]4[C:37]5[C:32](=[CH:33][C:34]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:36]=5)[CH2:31][CH2:30]4)[N:26]=[CH:25][N:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668943574-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 1-tert-butoxycarbonyl-pyrrolidin-3-yl ester

Product 1

HCID 498486594-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid pyrrolidin-3-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

21a was dissolved in 2.5 mL of DCM and 2.5 mL of TFA was added. The mixture was stirred at room temperature for 2 h then evaporated and the crude material was dissolved in DCM, washed with saturated NaHCO3 (3×10 mL), dried, filtered and evaporated to afford 21b.

Workup

  1. customthen evaporated
  2. dissolutionthe crude material was dissolved in DCM
  3. washwashed with saturated NaHCO3 (3×10 mL)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3b90abab7b5b433ca9cad3f61aea4d56
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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