2-(2-Aminoethyl)benzimidazole dihydrochloride → Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[2-[[2-(1H-benzimidazol-2-yl)ethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

HRID 54851

Reaction equation

HRID 54851 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([NH:14][C:15]([CH3:29])([C:26]([OH:28])=O)[CH2:16][C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[O:13])[CH2:8]2.Cl.Cl.[NH:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[CH2:41][CH2:42][NH2:43]>C(N(CC)CC)C>[NH:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[CH2:41][CH2:42][NH:43][C:26](=[O:28])[C:15]([NH:14][C:12](=[O:13])[O:11][CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[CH3:29]

Participants

4

Reactant 2

HCID 27880712-(2-Aminoethyl)benzimidazole dihydrochlorideHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophan

Product 1

HCID 86747494Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[2-[[2-(1H-benzimidazol-2-yl)ethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 70, the title compound was prepared from 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.33 g (1.41 mmol) of 1H-benzimidazole-2-ethanamine dihydrochloride with 0.5 mL of added triethylamine. The purified product after chromatography was obtained as a white foam, 0.38 g (56%); 1H NMR (CDCl3) δ1.46-1.91 (17H, m), 3.01-3.16 (2H, m), 3.27 (1H, d, J 15 Hz), 3.43 (1H, d, J 15 Hz), 3.58 (2H, m), 4.80 (1H, br s), 5.23 (1H, s), 6.67 (1H, m), 6.89-7.72 (10H, m), 8.28 (1H, br s).

Workup

  1. customThe purified product after chromatography was obtained as a white foam, 0.38 g (56%)

Sources & evidence

ORD record
ord-391b5d5066a74c0abd4cbb3d88442d64
Source dataset
uspto-grants-1997_04
Patent number
US05622983

Linked notes

Loading…