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

HRID 2214674Notes

Reaction equation

HRID 2214674 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[S:20][CH3:21])[CH3:11])=[O:9])[C:4](=[O:22])O1.[CH2:24]=O.[N:26]1([CH2:32][CH2:33][NH2:34])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:10]([CH3:11])[C:8]([C:7]2[CH2:24][N:34]([CH2:33][CH2:32][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:4](=[O:22])[C:5]=2[OH:6])=[O:9])=[C:14]([S:20][CH3:21])[CH:15]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 4082852-MorpholinoethylamineHCID 696563232-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methyl-acetamide

Product 1

HCID 547046804-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-fluoro-2-methylsulfanyl-benzyl)-methyl-amideYield 76%

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methyl-acetamide was reacted with paraformaldehyde and 2-morpholin-4-yl-ethylamine as described in Method 44B to give the title compound as a white solid (0.032 g, 76% yield). 1HNMR (300 MHz, CDCl3) δ: 7.07 (1H, dd, J=9.52, 6.23 Hz), 6.92 (1H, dd, J=9.52, 2.56 Hz), 6.82 (1H, td, J=8.06, 2.57 Hz), 4.61 (2H, s), 4.27 (2H, s), 3.95–3.90 (8H, m), 3.76–3.72 (2H, m), 3.39 (2H, t, J=5.85 Hz), 2.97 (3H, s), 2.47 (3H, s).

Sources & evidence

ORD record
ord-68541674212a4477b30c3cb4f7532fbd
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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