Formaldehyde → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-fluoro-2-methanesulfonyl-benzyl)-methoxy-amide

HRID 2214691Notes

Reaction equation

HRID 2214691 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[S:21]([CH3:24])(=[O:23])=[O:22])[O:11][CH3:12])=[O:9])[C:4](=[O:25])O1.[CH2:27]=O.[N:29]1([CH2:35][CH2:36][NH2:37])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8]([C:7]2[CH2:27][N:37]([CH2:36][CH2:35][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4](=[O:25])[C:5]=2[OH:6])=[O:9])=[C:15]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:16]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 4082852-MorpholinoethylamineHCID 738555712-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfonyl-benzyl)-N-methoxy-acetamide

Product 1

HCID 547046874-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-fluoro-2-methanesulfonyl-benzyl)-methoxy-amideYield 45%

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfonyl-benzyl)-N-methoxy-acetamide was reacted with paraformaldehyde and 2-morpholin-4-yl-ethylamine using the method described for the preparation of compound 767 to give the title compound as a white solid (0.021 g, 45% yield). 1HNMR (300 MHz, MeOD) δ: 7.75 (1H, dd, J=8.78, 2.93 Hz), 7.63–7.54 (2H, m), 5.34 (2H, s), 4.29 (2H, s), 4.01–3.99 (2H, m), 3.84–3.81 (2H, m), 3.77 (3H, s), 3.63–3.45 (6H, m), 3.39 (3H, s), 3.16–3.08 (2H, m).

Sources & evidence

ORD record
ord-84be106e139d41308465e1c4bc0eeea0
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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