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

HRID 2214690Notes

Reaction equation

HRID 2214690 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][CH3:22])[O:11][CH3:12])=[O:9])[C:4](=[O:23])O1.C=O.[N:27]1([CH2:33][CH2:34][NH2:35])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.Cl[C:37]1C=C(C=CC=1Cl)CN(C)C(C1CN(CCO)C(=O)C=1O)=O>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8]([C:7]2[CH2:37][N:35]([CH2:34][CH2:33][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:4](=[O:23])[C:5]=2[OH:6])=[O:9])=[C:15]([S:21][CH3:22])[CH:16]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 4082852-MorpholinoethylamineHCID 547046364-Hydroxy-1-(2-hydroxy-ethyl)-5-oxo-2,5 dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amideHCID 738555662-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methoxy-acetamide

Product 1

HCID 547046794-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-fluoro-2-methylsulfanyl-benzyl)-methoxy-amideYield 18%

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-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 (0.012 g, 18% yield). 1HNMR (300 MHz, CDCl3) δ: 7.27–7.22 (1H, m), 6.94 (1H, dd, J=9.51, 2.56 Hz), 6.83 (1H, td, J=8.42, 2.56 Hz), 4.95 (2H, s), 4.28 (2H, s), 3.97–3.75 (8H, m), 3.68 (3H, s), 3.40 (2H, t, J=5.85 Hz), 2.95 (2H, bs), 2.49 (3H, s).

Sources & evidence

ORD record
ord-ec37db6d7806485f89aa05435cfb744a
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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