Water → HCID 11554280, compound

HRID 749646Notes

Reaction equation

HRID 749646 reaction equation
Cl[C:2]1[S:3][C:4]([Cl:21])=[C:5]([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:20])([CH3:19])[C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[N:6]=1.[CH3:22][CH:23]1[CH2:27][CH2:26][CH2:25][NH:24]1.[OH2:28].CN(C=[O:33])C>>[Cl:21][C:4]1[S:3][C:2]([N:24]2[CH2:25][CH2:26][CH2:27][CH:23]2[CH3:22])=[N:6][C:5]=1[S:7]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:20])([CH3:19])[C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)(=[O:33])=[O:28]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 130032-MethylpyrrolidineHCID 68436149HCID 68436149, compound

Product 1

HCID 11554280HCID 11554280, compound

Procedure

To 2-(4-(2,5-dichlorothiazol-4-ylthio)phenyl)-1,1,1-trifluoropropan-2-ol (0.040 g, 0.098 mmol) in DMF (0.20 mL) was added 2-methylpyrolidine (0.022 mL, 0.22 mmol). The reaction was stirred for 2 h then poured into water (2 mL). The precipitate was filtered and purified by silica gel chromatography (elution with 30% ethyl acetate in hexanes) to provide 0.033 g of 2-(4-(5-chloro-2-(2-methylpyrrolidin-1-yl)thiazol-4-ylsulfonyl)phenyl)-1,1,1-trifluoropropan-2-ol. 1H NMR (400 MHz, CDCl3): δ 1.19 (d, J=6 Hz, 3H), 1.65-1.75 (m, 1H), 1.83 (s, 3H), 1.90-2.25 (m, 3H), 3.26-3.33 (m 1H), 3.40-3.45 (m, 1H), 3.90-3.96 (m, 1H), 7.78 (d, J=8 Hz, 2H), 8.11 (d, J=8 Hz, 2H).

Workup

  1. filtrationThe precipitate was filtered
  2. custompurified by silica gel chromatography (elution with 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9d37033e8d7448d98794e0254099655a
Source dataset
uspto-grants-2008_07
Patent number
US07402704B2

Reaction notes

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