Lithium Hydroxide → HCID 71078046, compound

HRID 1774485Notes

Reaction equation

HRID 1774485 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([C:21]3[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=3)[C:12]=2[CH3:27])[CH:7]=[N:6][CH:5]=1.[Li+].[OH-]>C1COCC1.CO>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([S:10][C:8]3[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=3)[C:3]([OH:28])=[O:2])=[C:12]([CH3:27])[N:13]2[C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71078166HCID 71078166, compound

Product 1

HCID 71078046HCID 71078046, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

5-[6-Chloro-2-methyl-1-(1-methyl-1H-pyrazol-4-yl)-1H-indol-3-ylsulfanyl]-nicotinic acid methyl ester (from the previous step) was dissolved in THF:MeOH (1:1, 4 mL) and LiOH (1 M aq., 2 mL) was added. After 15 minutes the reaction mixture was concentrated to dryness then purified via preparatory HPLC (10-100% ACN in H2O, 15 minute run, r.t.=8.21 minutes) to provide the desired product. Mass spectrometric data: [M−H]=397.

Workup

  1. concentrationAfter 15 minutes the reaction mixture was concentrated to dryness
  2. customthen purified via preparatory HPLC (10-100% ACN in H2O, 15 minute run, r.t.=8.21 minutes)

Sources & evidence

ORD record
ord-d41e2fc155b8430dbe1528f6cb098b12
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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