HCID 59135477, compound → HCID 178422551, compound

HRID 1993894Notes

Reaction equation

HRID 1993894 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=3[N:10]=[C:9]2[C:18]([OH:21])([CH3:20])[CH3:19])[CH2:4][CH2:3]1.[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH:27]([CH:32]=O)[CH2:26]2>>[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH:27]([CH2:32][NH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=4[N:10]=[C:9]3[C:18]([OH:21])([CH3:19])[CH3:20])[CH2:6][CH2:7]1)[CH2:26]2

Participants

3

Reactant 2

HCID 59135477HCID 59135477, compoundHCID 86620957HCID 86620957, compound

Product 1

HCID 178422551HCID 178422551, compound

Procedure

This compound was prepared from the hydrochloride salt of 2-[1-(4-amino-cyclohexyl)-5-methyl-1H-benzoimidazol-2-yl]-propan-2-ol (prepared as cis/trans-isomer mixture) and 5-chloro-indan-2-carbaldehyde. The less polar of the two substances isolated by chromatography gave cis-2-(1-{4-[(5-chloro-indan-2-ylmethyl)-amino]-cyclohexyl}-5-methyl-1H-benzoimidazol-2-yl)-propan-2-ol. The analysis of the 1H-NMR confirmed the cis-conformation of the cyclohexane. LC-MS showed a single peak, C27H34ClN3O (m/e) calcd 451.2390, obsd 452.3 (M+H). 1H-NMR (CD3OD) □ 7.83 (d, 1H), 7.40 (s, 1H), 7.20 (s, 1H), 7.17 (d, 1H), 7.10 (d, 1H), 7.03 (d, 1H), 5.32 (m, 1H), 3.16 (m, 2H), 2.96 (br s, 1H), 2.73-2.85 (m, 7H), 2.43 (s, 3H), 2.00 (m, 2H), 1.72 (s, 6H), 1.68 (m, 4H).

Workup

  1. customThe less polar of the two substances isolated by chromatography

Sources & evidence

ORD record
ord-a026871824b5415b862445fd771dc0a6
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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