HCID 22890468, compound → HCID 22890466, compound

HRID 896745Notes

Reaction equation

HRID 896745 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH:17]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)[CH2:18][NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])=[C:11]([N+:35]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pt]>[NH2:35][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[CH:17]([NH:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]#[N:34])=[CH:31][CH:32]=1)[CH2:18][NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21]

Participants

4

Reactant 1

HCID 22890468HCID 22890468, compound

Product 1

HCID 22890466HCID 22890466, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Propane-1-sulfonic acid [2-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-2-(4-cyano-phenylamino)-ethyl]-amide (0.250 g) was dissolved in ethanol (10 ml) and added to Pt/C (5%). The reaction was placed under a hydrogen atmosphere and stirred vigorously for 3 hours. The catalyst was filtered off and the product chromatographed (hexanes:ethyl acetate 1:2) to yield 133 mg of Propane-1-sulfonic acid [2-(2-amino-4-benzyloxy-5-methoxy-phenyl)-2-(4-cyano-phenylamino)-ethyl]-amide. 1HNMR(CDCl3): 7.3-7.45 (m, 7H), 6.71 (s, 1H), 6.52 (d, 2H), 6.3 (s, 1H), 5.33 (2, 1H), 5.08 (s, 2H), 5.0 (t, 1H), 4.42 (q, 1H), 3.75 (s, 3H), 3.70 (bs, 2H), 3.45 (t, 2H), 2.97 (m, 2H), 1.80 (m, 2H), 1.03 (t, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe product chromatographed (hexanes:ethyl acetate 1:2)

Sources & evidence

ORD record
ord-2c7b2cdb75f943de8b64aa1cb819f2e0
Source dataset
uspto-grants-2005_07
Patent number
US06919369B2

Reaction notes

Loading…