3-Hydroxyazetidine hydrochloride → HCID 25211810, compound

HRID 1409834Notes

Reaction equation

HRID 1409834 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[C:4]=1[CH3:16].Cl.[OH:20][CH:21]1[CH2:24][NH:23][CH2:22]1>>[OH:20][CH:21]1[CH2:24][N:23]([C:13]([C:11]2[S:12][C:8]([C:5]3[C:4]([CH3:16])=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:22]1

Participants

3

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 25211810HCID 25211810, compound

Procedure

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 3-hydroxyazetidine hydrochloride by the method described in Example 41. Colorless solid (78 mg, 73%). 1H NMR (DMSO-d6) 2.38 (s, 3H), 3.77-3.90 (m, 1H), 4.19-4.38 (m, 2H), 4.52-4.63 (m, 1H), 4.65-4.78 (m, 1H), 5.88 (d, J=5.9, 1H), 7.62 (d, J=4.0, 1H), 7.73 (d, J=4.0, 1H). 13C NMR 7.4, 58.9, 60.6, 62.5, 116.0 (q, J=2), 118.5 (q, J=271), 130.3, 130.5, 131.0, 140.2, 153.2 (q, J=40), 157.9, 160.8. 19F NMR −62.3. LC/MS 5.42 min, [M+1]+ 333.

Workup

  1. customLC/MS 5.42 min, [M+1]+ 333

Sources & evidence

ORD record
ord-810d39b4ca8346ab8a3e881bf3019e83
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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