Diisopropylethylamine → 2,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide

HRID 425801Notes

Reaction equation

HRID 425801 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[C:5]([C:7]([OH:9])=O)[N:6]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:48][CH:49]1[CH2:56][C@H:55]2[C@H:51]([CH2:52][NH:53][C@@H:54]2[CH2:57][NH:58][C:59](=[O:64])[C:60]([F:63])([F:62])[F:61])[CH2:50]1>CN(C=O)C.CC(=O)OCC.CC(=O)OCC.CCCCCCC.O>[F:63][C:60]([F:61])([F:62])[C:59]([NH:58][CH2:57][C@H:54]1[N:53]([C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[O:9])[CH2:52][C@H:51]2[C@@H:55]1[CH2:56][CH:49]([CH3:48])[CH2:50]2)=[O:64]

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 532718162-Methyl-5-m-tolyl-thiazole-4-carboxylic acidHCID 86643544N-[(1S,2S,5R)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 866435452,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

A solution of 2-methyl-5-m-tolyl-thiazole-4-carboxylic acid (1 g, 1 eq), DIPEA (3.7 mL, eq) and TBTU (1.4 g, 1 eq) in dry DMF (15 mL) was stirred at RT for 15 min. Then was added a solution of N-[(1S,2S,5R)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-2,2,2-trifluoro-acetamide (1.082 g, 1 eq) in dry DMF (15 mL). The resulting reaction mixture was stirred for 16 h, poured into water and diluted with EA. The org. phase was washed with a sat. aq. NaHCO3 solution, brine, dried over anh. MgSO4, filtered and concentrated to yield a crude yellow solid. FC (EA/n-heptane: 3/7 to 7/3) gave the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. washphase was washed with a sat. aq. NaHCO3 solution, brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a crude yellow solid

Sources & evidence

ORD record
ord-0d4f56c9f41b4263ac4431e2347c33e7
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

Loading…