Water → HCID 178438417, compound

HRID 521166Notes

Reaction equation

HRID 521166 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH:10]#[C:11][CH3:12].ON1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.[OH2:23]>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:2]([N:1]3[CH2:5][CH2:4][CH2:9][C@@H:10]4[C:19]5[CH:18]=[C:17]([C:6]#[C:7][CH3:8])[CH:22]=[CH:21][C:20]=5[CH2:12][C@H:11]34)=[O:23])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 6335PropyneHCID 757711-Hydroxybenzotriazole

Product 1

HCID 178438417HCID 178438417, compoundYield 30%

Procedure

The title compound is prepared from cis-1-(1-trifluoromethane-sulfonyl-1H-benzoimidazole-5-carbonyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester (mixture of isomers regarding sulfonyl group attachment to N-1 or N-3 of the benzimidazole) and propyne following a procedure analogous to that described in Example 155; in case the sulfonyl group on one of the benzimidazole nitrogens is not completely removed after the reaction, the mixture is treated with 1-hydroxy-benzotriazole and water. Yield: 30% of theory; LC (method 1): tR=2.92 min; Mass spectrum (ESI+): m/z=356 [m+H]+.

Workup

  1. additionmixture of isomers
  2. customin case the sulfonyl group on one of the benzimidazole nitrogens is not completely removed
  3. customafter the reaction

Sources & evidence

ORD record
ord-2de151a7bda9416796bf6dd758a2edf4
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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