Trifluoroacetic acid methylene chloride → HCID 22311996, compound

HRID 915096Notes

Reaction equation

HRID 915096 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[CH:19]=[N:20][CH:21]=[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>>[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:17]=3[NH:16][CH:15]=2)[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 69180928HCID 69180928, compound

Product 1

HCID 22311996HCID 22311996, compoundYield 158.1%

Procedure

4-(1H-Pyrrolo[3,2-c]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (2.0 g, 6.6 mmol) was set stirring in 1:1 TFA/CH2Cl2. After 45 min the mixture was evaporated and the golden oil brought up in Et2O. A solid formed and was filtered, washed with Et2O and air dried to give 2.1 g (100%) of a white solid as a TFA salt. MS (electrospray): exact mass calculated for C12H15N3, 201.13. m/z found, 202.1 [M++H]. 1H NMR (CDCl3, 400 MHz): 9.4 (br s, 1H), 8.96 (s, 1H), 8.26 (d, J=5.87 Hz, 1H), 7.24 (s, 1H), 6.99 (s, 1H), 3.22-3.16 (m, 2H), 3.05-2.95 (m, 1H), 2.86-2.77 (m, 2H), 2.05 (d, J=12.72 Hz, 2H), 1.89 (br s, 1H), 1.75-1.63 (m, 2H).

Workup

  1. customAfter 45 min the mixture was evaporated
  2. customA solid formed
  3. filtrationwas filtered
  4. washwashed with Et2O and air
  5. customdried

Sources & evidence

ORD record
ord-c5eda8a21ecd4d76b2a727b10f4332bb
Source dataset
uspto-grants-2007_09
Patent number
US07265102B2

Reaction notes

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