(S)-5-cyano-indan-2-carbaldehyde → HCID 178422555, compound

HRID 1993891Notes

Reaction equation

HRID 1993891 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.[CH:22]([C@@H:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:33]#[N:34])[CH:30]=2)[CH2:25]1)=O>>[OH:21][C:18]([C:9]1[N:8]([C@@H:5]2[CH2:4][CH2:3][C@H:2]([NH:1][CH2:22][C@@H:24]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:33]#[N:34])[CH:30]=4)[CH2:25]3)[CH2:7][CH2:6]2)[C:12]2[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=2[N:10]=1)([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 58852264(S)-5-cyano-indan-2-carbaldehydeHCID 59135477HCID 59135477, compound

Product 1

HCID 178422555HCID 178422555, 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 (S)-2-formyl-indan-5-carbonitrile through the same reductive amination method described previously. The crude mixture was separated through flash column chromatography using methylene chloride and methanol (20:1 to 10:1). The fraction with less retention time (higher Rf) gave cis-(S)-2-({4-[2-(1-hydroxy-1-methyl-ethyl)-5-methyl-benzoimidazole-1-yl]-cyclohexylamino}-methyl)-indan-5-carbonitrile. The analysis of the 1H-NMR confirmed the cis-conformation of the cyclohexane. LC-MS showed a single peak, C28H34N4O (m/e) calcd 442.2733, obsd 443.3 (M+H). 1H-NMR (CD3OD) □ 7.82 (d, 1H), 7.55 (s, 1H), 7.49 (d, 1H), 7.41 (s, 1H), 7.38 (d, 1H), 7.03 (d, 1H), 5.30 (m, 1H), 3.23 (m, 2H), 2.71-2.93 (m, 8H), 2.43 (s, 3H), 1.98 (br d, 2H), 1.72 (s, 6H), 1.64 (m, 4H).

Workup

  1. customThe crude mixture was separated through flash column chromatography

Sources & evidence

ORD record
ord-b1aba09204944239826d5bf17ce26e8d
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

Loading…