Acetyl chloride → HCID 56960649, compound

HRID 1626356Notes

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

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 prepared in step 1 of example 5 (524 mg, 0.000974 mol) in dichloromethane (20 ml), triethyl amine (1.35 ml, 0.00974 mol) was added followed by the addition of acetyl chloride (0.104 ml, 0.001461 mol) at 0° C. and the reaction mixture was stirred for 5 hrs at 30° C. Then reaction mixture was diluted with dichloromethane, washed with water, dried over calcium chloride and evaporated under reduced pressure to collect the crude product. The crude product was then purified by column chromatography using 1.5% methanol in chloroform as eluent to yield the 300 mg product as yellow solid.

Workup

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

Sources & evidence

ORD record: ord-3e264e7346c140cda6282e17fa88bd6f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785463B2

Reaction notes

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