Hydroxylamine → HCID 56932852, compound

HRID 1019663Notes

Reaction equation

HRID 1019663 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](/[CH:22]=[CH:23]/[C:24]([OH:26])=O)[CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2[N:46]([OH:47])N=NC=2C=1.ON.[OH-].[K+]>ClCCl>[OH:47][NH:46][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH:15][C:24](=[O:26])/[CH:23]=[CH:22]/[C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

8

Reactant 6

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 58055425HCID 58055425, compound

Product 1

HCID 56932852HCID 56932852, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in two steps according to Scheme 5 by (1) treating amine VII with (E)-3-pyridin-3-yl-acrylic acid, EDCI, HOBt, and TEA in dichloromethane, and (2) treating the ester intermediate with aqueous HONH2 and KOH. MS: calc'd (MH+) 338.1, exp (MH+) 338.4. 1H NMR (CD3OD, 400 MHz), 9.07 (s, 1H), 8.82 (m, 2H). 8.11 (m, 1H), 7.7 (m, 1H, J=15.6 Hz), 7.52 (m, 2H), 7.22 (m, 1H), 7.7 (d, 1H, J=16 Hz), 4.29 (m, 1H), 2.8-3.2 (m, 4H), 2.25 (m, 1H), 1.9 (m, 1H).

Sources & evidence

ORD record
ord-cc252db80cd04a319e7a7b66dfeb55c3
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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