Triethylamine → HCID 56960511, compound

HRID 1626355Notes

Reaction equation

[CH3:1][C:2]1[C:3]([O:15][C:16]2[CH:17]=[C:18]([CH:27]=[CH:28][CH:29]=2)/[CH:19]=[C:20]2/[C:21](=[O:26])[NH:22][C:23](=[O:25])[S:24]/2)=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH3:1][C:2]1[C:3]([O:15][C:16]2[CH:17]=[C:18]([CH:27]=[CH:28][CH:29]=2)/[CH:19]=[C:20]2/[C:21](=[O:26])[NH:22][C:23](=[O:25])[S:24]/2)=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH:9]1[CH2:10][CH2:11][N:12]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution Trifluoro acetate salt of (Z)-5-(3-((5-methyl-6-(piperidin-4-yloxy)pyrimidin-4-yl)oxy)benzylidene)thiazolidine-2,4-dione (524 mg, 0.000974 mol) in dichloromethane (20 ml), was added triethyl amine (1.35 ml, 0.00974 mol) followed by methane sulfonyl chloride (0.150 ml, 0.001461 mol) at 0° C. and reaction mixture was stirred for 2 hrs at 30° C. Then reaction mixture was diluted with dichloromethane and washed with water, dried over calcium chloride and evaporated under reduced pressure to collect the crude product. Then the crude product was purified by column chromatography using 1% methanol in chloroform as eluent to yield 300 mg product as white solid.

Workup

customreaction mixture
customThen reaction mixture
washwashed with water
dry with materialdried over calcium chloride
customevaporated under reduced pressure
customto collect the crude product
customThen the crude product was purified by column chromatography

Sources & evidence

ORD record: ord-4b4863a741d34d2e8eb6623d046bedf2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785463B2

Reaction notes

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