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

HRID 47522Notes

Reaction equation

HRID 47522 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[CH2:40][CH:39]([N:41]3[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=4[NH:43][C:42]3=[O:50])[CH2:38]2)[CH2:33][CH2:32]1)=[O:30].C(Cl)(=O)C.[CH3:55][S:56](Cl)(=[O:58])=[O:57]>>[CH3:27][O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([N:37]2[CH2:40][CH:39]([N:41]3[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=4[N:43]([S:56]([CH3:55])(=[O:58])=[O:57])[C:42]3=[O:50])[CH2:38]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 227452551-[1-(1-methoxycarbonylpiperidin-4-yl)-azetidin-3-yl]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 99093811-[1-(1-methoxycarbonylpiperidin-4-yl)-azetidin-3-yl]-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-4-yl)-azetidin-3-yl]-1,3-dihydro-2H-benzimidazol-2-one which was synthesized by the method of Referential Example 4 and that acetyl chloride was replaced with methanesulfonyl chloride. The title compound was obtained which was colorless and amorphous.

Workup

  1. customwas synthesized by the method of Referential Example 4

Sources & evidence

ORD record
ord-0f103733fc18474885f1b0f9261e953f
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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