Formaldehyde → HCID 54698189, compound

HRID 2214505Notes

Reaction equation

HRID 2214505 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(F)=CC=1)C.C=O.[C:22]1([CH2:28][CH2:29][NH2:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[F:31][C:32]1[CH:50]=[CH:49][C:35]([CH2:36][N:37]([CH3:48])[C:38]([C:40]2[CH2:41]N(C)[C:43](=[O:46])[C:44]=2[OH:45])=[O:39])=[CH:34][CH:33]=1>>[F:31][C:32]1[CH:50]=[CH:49][C:35]([CH2:36][N:37]([CH3:48])[C:38]([C:40]2[CH2:41][N:30]([CH2:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:43](=[O:46])[C:44]=2[OH:45])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1001PhenethylamineHCID 54698182N-[(4-fluorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 696556793-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester

Product 1

HCID 54698189HCID 54698189, compound

Procedure

3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 1-D) was treated with paraformaldehyde and 2-phenyl-ethylamine as described in the preparation of Compound 1. HRMS (M+H) calcd for C21H22FN2O3: 369.1615. found: 369.1625. 1H NMR (500 MHz, CDCl3) δ: 2.92 (overlapping m, 5), 3.74 (t, 2, J=7), 3.92 (s, 2), 4.56 (s, 2), 7.01–7.29 (overlapping m, 9). 13C NMR (125 MHz, CDCl3) δ: 34.45, 34.60, 44.70, 49.42, 51.46, 109.12, 115.66, 115.83, 126.75, 128.63, 128.72, 129.26, 129.33, 132.09, 132.11, 138.18, 153.11, 161.38, 163.34, 164.79, 166.18.

Sources & evidence

ORD record
ord-86e726325979433fbb3a7a837a1ef39b
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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