HCID 69334014, compound → HCID 69332353, compound

HRID 350404Notes

Reaction equation

HRID 350404 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:50])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][N:28]2[CH2:32][CH2:31][CH2:30][CH:29]2[CH2:33][O:34][C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][C:36]=2[N+:45]([O-])=O)=[O:26])=[CH:20][C:19]=1[O:48][CH3:49])C1C=CC=CC=1>CO.C1COCC1.[Pd]>[NH2:45][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:35]=1[O:34][CH2:33][CH:29]1[CH2:30][CH2:31][CH2:32][N:28]1[NH:27][C:25](=[O:26])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:16]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])=[O:50])=[C:19]([O:48][CH3:49])[CH:20]=1)[C:39]([O:41][CH3:42])=[O:40]

Participants

5

Reactant 1

HCID 69334014HCID 69334014, compound

Product 1

HCID 69332353HCID 69332353, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[1-[4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetamido]-2-pyrrolidinylmethoxy]-3-nitrobenzoate (1.52 g, 2.27 mmol) in MeOH (20 mL) and THF (5 mL) was hydrogenated over 5% Pd—C (wet, 52.2%; 1.21 g) under hydrogen atmosphere (4 kg/cm2) at room temperature After being stirred for 17 hr, the catalyst was filtered off and the filtrate was concentrated to dryness. Chromatography of the residue with EtOAc as eluent gave methyl 3-amino-4-[1-[4-[N′-(2-hydroxyphenyl)ureido]-3-methoxyphenylacetamido]-2-pyrrolidinylmethoxy]benzoate (1.12 g, 90%) as a brownish amorphous solid. 1H-NMR (CDCl3) δ 1.97–2.10 (m, 4H), 3.44 (s, 3H), 3.52–3.63 (m, 2H), 3.85 (s, 3H), 4.10–4.18 (m, 2H), 4.53 (m, 1H), 6.65–6.67 (m, 4H), 6.93–7.02 (m, 3H), 7.33 (d, J=2.2 Hz, 1H), 7.36 (dd, J=8.3, 2.2 Hz, 1H), 7.60 (s, 1H), 7.69 (d, J=8.3 Hz, 1H), 8.08 (s, 1H), 9.47 (broad s, 1H); FAB-MS m/z 549 (M++1).

Workup

  1. customat room temperature
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-45c34c0360194bdea54326430f1488ba
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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