Diethanolamine → HCID 86615470, compound

HRID 1989702Notes

Reaction equation

HRID 1989702 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[F:15][C:16]([F:50])([F:49])[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[N:20]=[C:19]([C:33]2[CH:34]=[C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([S:45](Cl)(=[O:47])=[O:46])[CH:40]=3)[CH:36]=[CH:37][CH:38]=2)[N:18]=1>C1COCC1>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[S:45]([C:41]1[CH:40]=[C:39]([C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([C:19]3[N:18]=[C:17]([C:16]([F:15])([F:49])[F:50])[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][CH:24]=4)[N:20]=3)[CH:34]=2)[CH:44]=[CH:43][CH:42]=1)(=[O:46])=[O:47]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 57468843HCID 57468843, compound

Product 1

HCID 86615470HCID 86615470, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (ice-water bath) and stirred mixture of diethanolamine (0.12 g, 1.14 mmol), triethylamine (0.06 ml, 0.42 mmol) and THF (2 ml) was added drop wise a solution of 3′-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-sulfonyl chloride (example 1.3) (0.21 g, 0.39 mmol) in THF (3 ml). The mixture was allowed to stir at room temperature for 16 h. Purification of the reaction mixture by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (diethyl ether/hexane) yielded the title compound as a white solid (0.125 g, 53%). MS (ISP) 611.6 [(M+H)+]; mp 111.5° C.

Workup

  1. stirringto stir at room temperature for 16 h
  2. customPurification of the reaction mixture by flash chromatography
  3. customon silica gel (ethyl acetate/heptane) and crystallization (diethyl ether/hexane)

Sources & evidence

ORD record
ord-b46cfff01a1f4c1e8ec1bf248380c802
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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