3-Furoic acid → HCID 178461996, compound

HRID 46160

Reaction equation

HRID 46160 reaction equation
[CH:1]1([NH:4][CH2:5][CH2:6][CH2:7][C:8]2([CH3:27])[S:12][C:11]([NH:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH3:15])=[N:10][C:9]2=[O:26])[CH2:3][CH2:2]1.[O:28]1[CH:32]=[CH:31][C:30]([C:33](O)=[O:34])=[CH:29]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:1]1([N:4]([CH2:5][CH2:6][CH2:7][C:8]2([CH3:27])[S:12][C:11]([NH:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:23])([F:25])[F:24])[CH3:15])=[N:10][C:9]2=[O:26])[C:33]([C:30]2[CH:31]=[CH:32][O:28][CH:29]=2)=[O:34])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 102683-Furoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178461995HCID 178461995, compound

Product 1

HCID 178461996HCID 178461996, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 5-(3-(cyclopropylamino)propyl)-5-methyl-2-((S)-1-(2-(trifluoromethyl)-phenyl)ethylamino)thiazol-4(5H)-one (0.106 g, 0.265 mmol), 3-furoic acid (0.0297 g, 0.265 mmol), TBTU (0.0895 g, 0.279 mmol), and N,N-diisopropylethylamine (0.0555 ml, 0.318 mmol) in DMF (3.0 mL) was stirred at ambient temp. overnight. The mixture was partitioned between EtOAc and Na2CO3 (aq), and the combined organic portions were washed with brine. The solvents were removed in vacuo, and the residue was purified by flash column chromatography (0 to 100% of EtOAc in hexanes) to give the title compound as a white solid. MS m/z: 494.1 (M+H)+.

Workup

  1. customThe mixture was partitioned between EtOAc and Na2CO3 (aq)
  2. washthe combined organic portions were washed with brine
  3. customThe solvents were removed in vacuo
  4. customthe residue was purified by flash column chromatography (0 to 100% of EtOAc in hexanes)

Sources & evidence

ORD record
ord-3ffbf3b2e5b44cd2845d9281c95246be
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Linked notes

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