2-(3-(methylamino)propyl)-1H-benzimidazole → HCID 10950195, compound

HRID 2394993Notes

Reaction equation

HRID 2394993 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH:12]([CH3:14])[CH3:13])[C:7]([CH2:16][C:17](O)=[O:18])([OH:15])[CH2:6][CH2:5]2.[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][CH2:30][CH2:31][NH:32][CH3:33]>>[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][CH2:30][CH2:31][N:32]([CH3:33])[C:17](=[O:18])[CH2:16][C@@:7]1([OH:15])[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[C@@H:8]1[CH:12]([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 31454002-(3-(methylamino)propyl)-1H-benzimidazoleHCID 18974378(6-Fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid

Product 1

HCID 10950195HCID 10950195, compound

Procedure

An "activated derivative" of (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl) acetic acid is a derivative that renders the acid more active in the reaction with [3-(1H-benzimidazol-2-yl)propyl]methylamine to form (1S,2S)-N-[3-(1H-benzimidazol-2-yl) propyl]-2-(6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylacetamide. Typical such derivatives include the corresponding acyl halides and anhydrides, and a preferred activated derivative is the mixed anhydride of(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetic acid with trimethylacetic acid.

Sources & evidence

ORD record
ord-1260ba7e94c443d08984ddf66ca27fbf
Source dataset
uspto-grants-1998_09
Patent number
US05811556

Reaction notes

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