Trifluoroacetic acid methylene chloride → HCID 22311992, compound

HRID 1370050Notes

Reaction equation

HRID 1370050 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[CH:19]=[N:20][C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:22][C:17]=3[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[N:23]1([C:21]2[N:20]=[CH:19][C:18]3[C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[CH:15][NH:16][C:17]=3[CH:22]=2)[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 69182577HCID 69182577, compound

Product 1

HCID 22311992HCID 22311992, compoundYield 100.1%

Procedure

4-(6-Morpholin-4-yl-1H-pyrrolo[3,2-c]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (380 mg, 0.98 mmol) was set stirring in 1:1 TFA/CH2Cl2. After 45 min the mixture was evaporated. The residue was dissolved in MeOH (20 mL) and neutralized with DOWEX 550A OH anion exchange resin to pH 8. The resin was then filtered off and MeOH was removed under reduced pressure to give 281 mg (100%) of a yellow solid. MS (electrospray): exact mass calculated for C16H22N4O, 286.18; m/z found, 287.1 [M++H].

Workup

  1. customAfter 45 min the mixture was evaporated
  2. dissolutionThe residue was dissolved in MeOH (20 mL)
  3. filtrationThe resin was then filtered off
  4. customMeOH was removed under reduced pressure

Sources & evidence

ORD record
ord-484d1d062a1346069d2eba0c8cc2efe6
Source dataset
uspto-grants-2003_06
Patent number
US06579896B2

Reaction notes

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