5-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one → N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide

HRID 132585Notes

Reaction equation

HRID 132585 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[C:22]([O:30][CH2:31][C@@H:32]2[CH2:34][O:33]2)[CH:21]=1>>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:34][C@H:32]([OH:33])[CH2:31][O:30][C:22]4[CH:21]=[C:20]([O:19][CH3:18])[CH:25]=[CH:24][C:23]=4[NH:26][C:27](=[O:29])[CH3:28])[CH2:14][CH2:15]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 137921045-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 71570340N-{4-Methoxy-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

Product 1

HCID 69199245N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide

Procedure

The title compound was prepared according to the procedure described in Example 30 above from 5-fluoro-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one and N-{4-methoxy-2-[(2S)oxiranylmethoxy]phenyl}acetamide. The product was purified by preparative HPLC (Kromasil column; eluent: acetonitrile/water) to afford a colourless solid (84%).

Workup

  1. customThe product was purified by preparative HPLC (Kromasil column; eluent: acetonitrile/water)

Sources & evidence

ORD record
ord-a0e10a1942e94598870e60370b5f682a
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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