HCID 18926562, compound → HCID 18926572, compound

HRID 1600194Notes

Reaction equation

HRID 1600194 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16]([CH2:30][N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1)=[C:17]([CH3:29])[N:18]2[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=O)C1C=CC=CC=1>O1CCCC1.[Pd]>[NH2:11][CH2:12][CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16]([CH2:30][N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1)=[C:17]([CH3:29])[N:18]2[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 1

HCID 18926562HCID 18926562, compound

Product 1

HCID 18926572HCID 18926572, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenation of methyl 4-(2-benzyloxycarbonylaminoethyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indole-1-propanoate (0.50 g) in tetrahydrofuran (20 ml) in the presence of 10% palladium on carbon (100 mg+a further 50 mg quantities after 24 and 48hours) for 72 hours, followed by work up as described for Preparation 32 gave the title compound as a gum (0.20 g), Rf. 0.15(SS3). δ(CDCl3): 1.70(2H,br), 2.47(3H,s), 2.81(2H,t), 2.88(4H,s), 3.70(3H,s), 4.48(2H,t), 5.37(2H,s), 6.86(1H,s), 6.95(1H,d), 7.04(1H,s), 7.17(1H,m), 7.24(1H,d), 7.42(1H,s).

Workup

  1. customas described for Preparation 32

Sources & evidence

ORD record
ord-a64cba131d7b4e2387c0466a18f99bb0
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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