Lithium Hydroxide → HCID 21901285, compound

HRID 1064181Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:10]=1)=[O:5])C.[Li+].[OH-]>>[CH3:21][N:18]1[CH2:17][CH2:16][N:15]([C:11]2[CH:10]=[C:9]([CH:7]3[CH2:8][CH:6]3[C:4]([OH:5])=[O:3])[CH:14]=[CH:13][CH:12]=2)[CH2:20][CH2:19]1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 58736981HCID 58736981, compound

Product 1

HCID 21901285HCID 21901285, compound

Procedure

In a manner similar to that described for step 3 of Example 172, Intermediate 173(a) was treated with 1 M aqueous LiOH to give crude 2-[3-(4-methyl-piperazin-1-yl)-phenyl]-cyclopropanecarboxylic acid. Crude 2-[3-(4-methyl-piperazin-1-yl)-phenyl]-cyclopropanecarboxylic acid was coupled to the title compound of Example 2 (71 mg, 0.3 mmol) also in a manner similar to that described for step 3 of Example 172. Extractive work-up from ethyl acetate and saturated aqueous NaHCO3 afforded the crude product, which was purified by silica gel chromatography, eluting with 3% MeOH\CH2Cl2, to furnish the title compound (38 mg, 0.086 mmol) in 22% yield.

Sources & evidence

ORD record: ord-81e04ce39ca24160bcb165a3ea889e14
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967198B2

Reaction notes

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