5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid → HCID 131729829, compound

HRID 1409854Notes

Reaction equation

HRID 1409854 reaction equation
FC(F)(F)C1ON=C(C2SC(C(O)=O)=CC=2)C=1C.CN(C[C@H]1CCCNC1)C(=O)OC(C)(C)C.[ClH:35].[CH3:36][NH:37][C@@H:38]1[CH2:43][CH2:42][CH2:41][N:40]([C:44]([C:46]2[S:47][C:48]([C:51]3[C:55]([CH3:56])=[C:54]([C:57]([F:60])([F:59])[F:58])[O:53][N:52]=3)=[CH:49][CH:50]=2)=[O:45])[CH2:39]1>>[ClH:35].[CH3:36][NH:37][C@H:38]1[CH2:43][CH2:42][CH2:41][N:40]([C:44]([C:46]2[S:47][C:48]([C:51]3[C:55]([CH3:56])=[C:54]([C:57]([F:60])([F:59])[F:58])[O:53][N:52]=3)=[CH:49][CH:50]=2)=[O:45])[CH2:39]1

Participants

4

Reactant 3

HCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acidHCID 26966964tert-butyl (S)-methyl(piperidin-3-ylmethyl)carbamateHCID 131729830HCID 131729830, compound

Product 1

HCID 131729829HCID 131729829, compound

Procedure

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and tert-butyl methyl[(3S)-piperidin-3-ylmethyl]carbamate (Preparative Example 36, presumed quantitative yield, 4.48 mmol) in the same manner as the 3R isomer (Example 93) to afford Boc-protected intermediate as a colorless oil (1.51 g, 71%). LC/MS 7.32 min, [M+1]+ 474. The product was obtained as a colorless free-flowing powder (1.06 g, 81%, some loss of material had occurred on rotary evaporation). LC/MS 4.55 min, [M+1]+ 374.

Workup

  1. customto afford Boc-
  2. customLC/MS 7.32 min, [M+1]+ 474
  3. customThe product was obtained as a colorless free-flowing powder (1.06 g, 81%
  4. customsome loss of material had occurred on rotary evaporation)
  5. customLC/MS 4.55 min, [M+1]+ 374

Sources & evidence

ORD record
ord-ea7bc5648174432cb9cea9c5199d3187
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

Loading…