Sodium hydride → HCID 118093743, compound

HRID 625713Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:17]([C:18]#[N:19])=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C@H:13]3[O:20][C:21]2[CH:26]=[CH:25][C:24]([C@H:27]3[CH2:29][C@@H:28]3[C:30]([OH:32])=[O:31])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:35][O-:36].[Na+]>CO>[C:18]([C:17]1[C:9]([CH2:8][C:5]2[CH:6]=[N:7][C:2]([O:36][CH3:35])=[CH:3][CH:4]=2)=[C:10]2[C:14](=[CH:15][CH:16]=1)[C@H:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C@H:27]3[CH2:29][C@@H:28]3[C:30]([OH:32])=[O:31])=[CH:25][CH:26]=1)[CH2:12][CH2:11]2)#[N:19]

Participants

Conditions

Temperature: 90 °C

Procedure

(1S,2S)-2-{4-[(R)-4-(6-Chloro-pyridin-3-ylmethyl)-5-cyano-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid (Example 40, 100 mg, 0.22 mmol) is suspended in methanol (10 mL) and sodium hydride (60% in mineral oil, 27 mg, 0.67 mmol) is added. After 6 hours at 90° C. sodium methoxide (130 mg, 2.25 mmol) is added and the mixture stirred for 24 hours at 90° C. The solvent is removed under vacuum and the residue is purified by flash chromatography (0-10% MeOH in CH2Cl2) to give the title compound (Yield: 13 mg). LC (METHOD 3): tR=4.04 min; Mass spectrum (ES+): m/z=441 [M+H]+.

Workup

customThe solvent is removed under vacuum
customthe residue is purified by flash chromatography (0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-07c8d241da0e4219ba5a1166fb56d9f2
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09308194B2

Reaction notes

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