Sodium hydride → HCID 118094090, compound

HRID 515536Notes

Reaction equation

HRID 515536 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([S:12]([NH:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)(=[O:14])=[O:13])=[CH:7][C:6]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])=[CH:5][C:4]=2[N:3]=1.[CH:28]1([CH2:31][OH:32])[CH2:30][CH2:29]1.[H-].[Na+]>>[CH:16]1([NH:15][S:12]([C:8]2[C:9]3[CH:10]=[CH:11][C:2]([O:32][CH2:31][CH:28]4[CH2:30][CH2:29]4)=[N:3][C:4]=3[CH:5]=[C:6]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:7]=2)(=[O:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 118094028HCID 118094028, compound

Product 1

HCID 118094090HCID 118094090, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamide (18 mg, 0.044 mmol) and cyclopropylmethanol (1 mL) was treated with excess sodium hydride and heated to 60° C. overnight. The mixture was concentrated and purified by preparative HPLC to give the desired product, N-cyclopentyl-2-(cyclopropylmethoxy)-7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamide.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5759365e4cc248b0867f54dec9a10f33
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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