Hydrochloric Acid → 2-Amino-6-({[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}thio)-4-(4-{[(2S)-2-hydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

HRID 508178Notes

Reaction equation

HRID 508178 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@@H:18]([O:20][Si](C(C)(C)C)(C)C)[CH3:19])=[CH:12][CH:11]=2)[C:5]([C:28]#[N:29])=[C:4]([S:30][CH2:31][C:32]2[N:33]=[C:34]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[O:35][C:36]=2[CH3:37])[N:3]=1.Cl>CO>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][C@@H:18]([OH:20])[CH3:19])=[CH:14][CH:15]=2)[C:5]([C:28]#[N:29])=[C:4]([S:30][CH2:31][C:32]2[N:33]=[C:34]([C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)[O:35][C:36]=2[CH3:37])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 672153962-Amino-4-(4-{[(2S)-2-{[tert-butyl(dimethyl)silyl]oxy}propyl]oxy}phenyl)-6-({[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}thio)pyridine-3,5-dicarbonitrile

Product 1

HCID 672154052-Amino-6-({[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}thio)-4-(4-{[(2S)-2-hydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

65 mg (0.10 mmol) of the compound from Example 95A are dissolved in 4 ml of methanol, and 1.5 ml of 1 N hydrochloric acid are added. The mixture is stirred at RT for 12 h. The solvent is then removed on a rotary evaporator, and the residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). After removal of the solvent on a rotary evaporator, the product is obtained as a white solid.

Workup

  1. customThe solvent is then removed on a rotary evaporator
  2. customthe residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  3. customAfter removal of the solvent
  4. customon a rotary evaporator
  5. customthe product is obtained as a white solid

Sources & evidence

ORD record
ord-d571b6ae41104c8b8d77d168d4dfc37b
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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