Hydroxylamine → HCID 56932960, compound

HRID 1019673Notes

Reaction equation

HRID 1019673 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].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](Cl)(=[O:24])=[O:23])[CH:17]=1.[OH:26][NH2:27].[OH-].[K+]>ClCCl>[OH:26][NH:27][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH:15][S:22]([C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)(=[O:24])=[O:23])[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 3164136Pyridine-3-sulfonyl chlorideHCID 58055425HCID 58055425, compound

Product 1

HCID 56932960HCID 56932960, 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 pyridine-3-sulfonyl chloride and TEA in dichloromethane, and (2) treating the ester intermediate with aqueous HONH2 and KOH. MS: calc'd (MH+) 348, exp (MH+) 348.4. 1H NMR (CD3OD, 400 MHz), 9.05 (s, 1H), 8.80 (d, 1H, J=4.4 Hz), 7.31 (d, 1H, J=8.0 Hz), 7.65 (m, 1H), 7.47 (d, 1H, J=8.0 Hz), 7.36 (s, 1H), 7.16 (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-fadc2f5c8dba4d45a6030166ecc1ed8c
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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