Acetyl chloride → 1-(1-methoxycarbonylpiperidin-4-yl-piperidin-4-yl]-4-fluoro-3-(methylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 47524Notes

Reaction equation

HRID 47524 reaction equation
COC(N1CCC(N2CCC(N3C4C=CC=CC=4NC3=O)CC2)CC1)=O.[CH3:27][O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([N:37]2[CH2:42][CH2:41][CH:40]([N:43]3[C:47]4[CH:48]=[CH:49][CH:50]=[C:51]([F:52])[C:46]=4[NH:45][C:44]3=[O:53])[CH2:39][CH2:38]2)[CH2:33][CH2:32]1)=[O:30].C(Cl)(=O)C.[CH3:58][S:59](Cl)(=[O:61])=[O:60]>>[CH3:27][O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([N:37]2[CH2:38][CH2:39][CH:40]([N:43]3[C:47]4[CH:48]=[CH:49][CH:50]=[C:51]([F:52])[C:46]=4[N:45]([S:59]([CH3:58])(=[O:61])=[O:60])[C:44]3=[O:53])[CH2:41][CH2:42]2)[CH2:33][CH2:32]1)=[O:30]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 31297Methanesulfonyl chlorideHCID 227452181-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-oneHCID 227452491-[1-(1-methoxycarbonylpiperidin-4yl)-piperidin-4-yl]-4-fluoro-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 99117911-(1-methoxycarbonylpiperidin-4-yl-piperidin-4-yl]-4-fluoro-3-(methylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one

Procedure

Example 12 was repeated except that the 1-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one was replaced with 1-[1-(1-methoxycarbonylpiperidin-4yl)-piperidin-4-yl]-4-fluoro-1,3-dihydro-2H-benzimidazol-2-one which was synthesized by the method of Referential Example 6 and that acetyl chloride was replaced with methanesulfonyl chloride. The title compound was obtained as a colorless oil.

Workup

  1. customwas synthesized by the method of Referential Example 6

Sources & evidence

ORD record
ord-a30e8f9e36564d99aae738df86ac3d81
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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