2-(Phenylcarbamoyl)acetic acid → HCID 11199503, compound

HRID 1373081Notes

Reaction equation

HRID 1373081 reaction equation
[C:1]1([NH:7][C:8](=[O:13])[CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][N:15]([CH2:19][C@@H:20]([NH:27][CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][CH2:17][OH:18]>>[OH:18][CH2:17][CH2:16][N:15]([CH3:14])[CH2:19][C@@H:20]([N:27]([CH3:28])[C:10](=[O:12])[CH2:9][C:8]([NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 2565932-(Phenylcarbamoyl)acetic acidHCID 58780858HCID 58780858, compound

Product 1

HCID 11199503HCID 11199503, compound

Procedure

Coupling of the N-phenyl-malonamic acid (394 mg, 2.2 mmol) with 2-[methyl-(2-methylamino-(S)-2-phenyl-ethyl)-amino]-ethanol from step b above (562 mg, 2.0 mmol) using the general coupling method A yielded compound 21 (620 mg, 84%). 1H NMR (400 MHz, DMSO-d6) δ: 10.14, 10.11 (2s, total 1H), 7.60 (d, 2H), 7.31 (m, 7H), 7.05 (t, 1H), 5.82, 5.12 (m, total 1H), 4.41, 4.35 (2t, total 1H), 3.72–3.46 (m, 4H), 2.95–2.50 (m, 7H), 2.31, 2.26 (2s, total 3H); MS: [M+1]+: 370.

Sources & evidence

ORD record
ord-bff340c56a7a4e799830d542211b0e3c
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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