Diisopropylethylamine → HCID 86662769, compound

HRID 2359728Notes

Reaction equation

HRID 2359728 reaction equation
[I:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][S:5]([NH:8][C:9]1[N:10]=[CH:11][S:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:7])=[O:6].C(N(CC)C(C)C)(C)C.FC(F)(F)S(O[CH2:37][CH:38]([F:40])[F:39])(=O)=O>C(#N)C>[F:39][CH:38]([F:40])[CH2:37][N:8]([S:5]([CH2:4][C:3]1[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=1[I:1])(=[O:7])=[O:6])[C:9]1[N:10]=[CH:11][S:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 66605621HCID 66605621, compound

Product 1

HCID 86662769HCID 86662769, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2.1 g (4.8 mmol) of methyl 4-{[(2-iodobenzyl)sulfonyl]amino}-1,3-thiazole-5-carboxylate were dissolved in 20 ml of acetonitrile, and 0.9 ml (5.3 mmol) of N,N-diisopropylethylamine was added at RT. The reaction mixture was stirred at RT for 5 min and then a solution of 1.54 g (7.2 mmol) of difluoroethyl trifluoromethane-sulfonate in 5 ml of acetonitrile was added dropwise within 10 min. The reaction mixture was stirred at RT for 12 h and then concentrated to dryness. The residue was purified by means of preparative HPLC(C18—SiO2, gradient acetonitrile/water 20:80 to 100:0). This gave 2.09 g of methyl 4-{(2,2-difluoroethyl)[(2-iodobenzyl)-sulfonyl]amino}-1,3-thiazole-5-carboxylate.

Workup

  1. stirringThe reaction mixture was stirred at RT for 12 h
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by means of preparative HPLC(C18—SiO2, gradient acetonitrile/water 20:80 to 100:0)

Sources & evidence

ORD record
ord-1d2f885565034d31910897230f5d2dfb
Source dataset
uspto-grants-2014_04
Patent number
US08686000B2

Reaction notes

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