HCID 22181351, compound → HCID 22181262, compound

HRID 1796512Notes

Reaction equation

HRID 1796512 reaction equation
[CH3:1][N:2]([C:25]([NH:27][CH:28]([CH3:30])[CH3:29])=[O:26])[C:3]1[CH:4]=[CH:5][C:6]([N+:22]([O-])=O)=[C:7]([NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)[CH:8]=1>CCOC(C)=O.[Pd]>[NH2:22][C:6]1[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[C:25]([NH:27][CH:28]([CH3:29])[CH3:30])=[O:26])=[CH:8][C:7]=1[NH:9][C:10](=[O:21])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH3:20])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 22181351HCID 22181351, compound

Product 1

HCID 22181262HCID 22181262, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[5-[methyl[[isopropylamino]carbonyl]amino]-2-nitrophenyl]4-ethoxy-benzeneacetamide (190 mg, 0.46 mmol) and 10% Pd/C in EtOAc (5.0 mL) was hydrogenated for 4 hours at 30 psi. The contents were filtered through Celite, and the Celite was washed with EtOAc (2×10.0 mL). The solvent was removed in vacuo to provide the title compound (170 mg, 99%), which was used without further purification. 1HNMR (400 MHz, CDCl3): δ 0.98 (d, J=6.5 Hz, 6H), 1.38 (t, J=7.1 Hz, 3H), 3.09 (s, 3H), 3.69 (s, 2H), 3.86 (spt, J=6.7 Hz, 1H), 3.99 (q, J=7.0 Hz, 2H), 4.11–4.13 (m, 1H), 6.71 (d, J=8.4 Hz, 1H), 6.82 (dd, J=2.4 Hz, J=8.4 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 6.96 (d, J=2.3 Hz, 1H), 7.24 (d, J=8.6 Hz, 2H), 7.58 (s, 1H). MS (ESI) (M+H)+=385. 50C: N-[2-(4-ethoxybenzyl)-1-[(2S)-2-pyrrolidinylmethyl]-1H-benzimidazol-5-yl]-N′-N-(1-isopropyl)urea

Workup

  1. filtrationThe contents were filtered through Celite
  2. washthe Celite was washed with EtOAc (2×10.0 mL)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-13cdc725f14246e9a3ab6548135f9680
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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