Formic Acid → HCID 52920283, compound

HRID 1193197Notes

Reaction equation

HRID 1193197 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][N:14]([C:17]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[C:26]4[N:30](C5CCCCO5)[N:29]=[CH:28][CH:27]=4)=[O:18])[CH2:15]3)[CH2:10]2)[N:3]=1.Cl.C(O)=O>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][N:14]([C:17]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[C:26]4[NH:30][N:29]=[CH:28][CH:27]=4)=[O:18])[CH2:15]3)[CH2:10]2)[N:3]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 67116832HCID 67116832, compound

Product 1

HCID 52920283HCID 52920283, compoundYield 100%

Procedure

(1R,6S)-8-(4,6-Dimethylpyrimidin-2-yl)-3-({5-fluoro-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]phenyl}carbonyl)-3,8-diazabicyclo[4.2.0]octane (8 mg, 0.017 mmol) was combined with 6 M aq. HCl (8.154 mL, 0.05 mmol) in formic acid (2.5 mL, 0.75 mmol) and stirred for 90 min. The reaction mixture was concentrated from MeON (3×12 mL), then the mixture was dissolved in NH3 MeON and concentrated to neutralize acid. The residue was dissolved in CHCl3 and purified by FCC to afford the title compound (6.7 mg, 100%). MS (ESI) mass calcd. for C22H23FN6O, 406.5; m/z found, 407.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated from MeON (3×12 mL)
  2. dissolutionthe mixture was dissolved in NH3 MeON
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in CHCl3
  5. custompurified by FCC

Sources & evidence

ORD record
ord-ac81f64a1bbf4380a49df3eb54db6778
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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