Formic Acid → HCID 86669026, compound

HRID 2366303Notes

Reaction equation

HRID 2366303 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]2[C:12]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23][N:22]=3)=[N:13][CH:14]=[C:15]([C:18]#N)[C:16]=2[N:17]=1.C(O)=[O:29]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]2[C:12]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23][N:22]=3)=[N:13][CH:14]=[C:15]([CH:18]=[O:29])[C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 66801722HCID 66801722, compound

Product 1

HCID 86669026HCID 86669026, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(2-chloro-6-fluoro-phenyl)-4-[(6-methylpyrimidin-4-yl)amino]thiazolo[5,4-c]pyridine-7-carbonitrile (0.0500 mmol, 61.8 mg) in formic acid (2.25 mL) and water (0.75 mL) was added Al—Ni Alloy (130 mg). The mixture was heated at 100° C. for 4 hours. The mixture was then cooled to room temperature and filtered through celite, washed with 95% EtOH, concentrated via rotavap to give a yellow solid which was used in the next step without purification. LCMS (ESI) m/z 400.1 [M+H+].

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through celite
  3. washwashed with 95% EtOH
  4. concentrationconcentrated via rotavap
  5. customto give a yellow solid which
  6. customwas used in the next step without purification

Sources & evidence

ORD record
ord-9ef7861269714ee3a87a22743dad0a72
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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