Hydroxylamine → HCID 56932910, compound

HRID 1019668Notes

Reaction equation

HRID 1019668 reaction equation
CO[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH2:15])[CH2:8][C:7]=2[CH:6]=1)=[O:4].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.[OH:30][NH2:31].[OH-].[K+]>ClCCl>[OH:30][NH:31][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH:15][S:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:29])([F:28])[F:16])[CH:19]=3)(=[O:26])=[O:25])[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 58055425HCID 58055425, compound

Product 1

HCID 56932910HCID 56932910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in two steps according to Scheme 6 by (1) treating amine VII with 3-trifluoromethyl-benzenesulfonyl chloride and TEA in dichloromethane, and (2) treating the ester intermediate with aqueous HONH2 and KOH. MS: calc'd (MH+) 415, exp (MH+) 415.4. 1H NMR (CD3OD, 400 MHz), 8.20 (s, 1H), 8.18 (d, 1H, J=8.8 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.82 (t, 1H, J=7.6 Hz), 7.46 (d, 1H, J=7.6 Hz), 7.36 (s, 1H), 7.15 (d, 1H, J=8.0 Hz), 3.55 (m, 1H), 2.95 (m, 2H), 2.82 (m, 1H), 2.69 (m, 1H), 1.95 (m, 1H) 1.73 (m, 1H).

Sources & evidence

ORD record
ord-20a9124cbf394dd088cc4996f14e4d21
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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