Ethanolamine → HCID 69882922, compound

HRID 2120346Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:6]([Cl:31])=[C:7]([NH:21][C:22](=[O:30])[C@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])[CH:8]=[CH:9][C:10]=1[S:11]([C:14]1[CH:19]=[CH:18][C:17](F)=[CH:16][CH:15]=1)(=[O:13])=[O:12])(=[O:3])[CH3:2].[CH2:32]([CH2:34][NH2:35])[OH:33]>C(#N)C>[C:1]([NH:4][C:5]1[C:6]([Cl:31])=[C:7]([NH:21][C:22](=[O:30])[C@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:25])[F:26])[CH:8]=[CH:9][C:10]=1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:35][CH2:34][CH2:32][OH:33])=[CH:16][CH:15]=1)(=[O:12])=[O:13])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

(R)-N-[3-Acetamido-2-chloro-4-(4-fluorophenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (683 mg) (Example 10), ethanolamine (177 mg, 2 eq) and acetonitrile (6 ml) were stirred and heated (85° C.) under argon for 24 hours. The solvent was removed and the residual gum was redissolved in MeOH (10 ml) and poured onto deactivated silica (5 g). This was concentrated to give a free flowing powder which was transferred to the top of an ISOLUTE column (50 g silica). This was chromatographed, eluting with MeOH/DCM to give the title compound (247 mg) as a brown solid. NMR (400 MHz): 1.59 (s, 3H), 1.95 (s, 3H), 3.08-3.19 (m, 2H), 3.53 (q, 2H), 4.66-4.73 (t, 1H), 6.62 (d, 2H), 6.67 (t, 1H), 7.0 (brs, 1H), 7.44 (d, 2H), 8.06 (d, 1H), 8.29 (d, 1H), 9.61 (brs, 1H), 9.82 (brs, 1H); m/z 524 (M+H)+.

Workup

customThe solvent was removed
dissolutionthe residual gum was redissolved in MeOH (10 ml)
additionpoured
concentrationThis was concentrated
customto give
customThis was chromatographed
washeluting with MeOH/DCM

Sources & evidence

ORD record: ord-37460f12406140929bf79a2b73cf8d3a
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689909B1

Reaction notes

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