Formaldehyde → HCID 54698188, compound

HRID 2214504Notes

Reaction equation

HRID 2214504 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(F)=CC=1)C.C=O.[N:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH2:30])=[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:25]3[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=3)[C:43](=[O:46])[C:44]=2[OH:45])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 832754-PyridineethanamineHCID 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 54698188HCID 54698188, compound

Procedure

3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 1-D) was treated with paraformaldehyde and 2-pyridin-4-yl-ethylamine as described in the preparation of Compound 1. HRMS (M+H) calcd for C20H21FN3O3: 370.1567. found: 370.1568. 1H NMR (500 MHz, CDCl3) δ: 3.00 (s, 3), 3.23 (t, 2, J=7), 3.90 (t, 2, J=7), 4.20 (s, 2), 4.60 (s, 2), 7.03 (m, 2), 7.21 (m, 2), 7.80 (d, 2, J=6), 8.73 (d, 2, J=6). 13C NMR (125 MHz, CDCl3) δ: 34.55, 34.63, 42.47, 49.04, 51.55, 109.53, 114.58, 115.74, 115.91, 127.10, 129.30, 129.50, 131.76, 141.92, 153.22, 158.36, 160.92, 161.23, 161.43, 163.40, 165.33, 166.13.

Sources & evidence

ORD record
ord-504f7bd996214851bf4e8f324f535cbd
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

Loading…