Water → HCID 178491496, compound

HRID 1754073Notes

Reaction equation

HRID 1754073 reaction equation
[CH:1]1([NH:6][C:7]2[N:11]3[N:12]=[CH:13][C:14]([C:15]#[N:16])=[C:10]3[NH:9][C:8]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[F:25])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:26]>CS(C)=O>[NH2:9][C:10]1[N:11](/[C:7](=[N:6]/[CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)/[C:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[F:25])=[O:26])[N:12]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 962WaterHCID 178489025HCID 178489025, compound

Product 1

HCID 178491496HCID 178491496, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A light yellow solution of 3-(cyclopentylamino)-2-(2-fluoro-4-methoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (199 mg, 0.586 mmol) in DMSO (100 mL) was stored for several days at RT. After 2 days, it became a light brown solution and this solution was stored for 50 days. Then, it was poured into water (300 mL) and the organic compound was extracted into ethyl acetate (3×50 mL). The combined organic extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave the crude yellow solid which was purified using an ISCO (80 g) column chromatography eluting with 0-50% ethyl acetate in hexanes. The desired fractions were combined and the solvent was removed under vacuum to isolate 32 mg (15.4% yield) of (E)-5-amino-1-(1-(cyclopentylimino)-2-(2-fluoro-4-methoxyphenyl)-2-oxo ethyl)-1H-pyrazole-4-carbonitrile as an yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.45-1.53 (br m, 4H), 1.53-1.85 (br m, 4H), 3.73 (p, 1H), 3.89, (s, 3H), 6.95-7.10 (m, 2H), 7.72 (s, 1H), 7.92 (t, J=8.5 Hz, 1H), 8.11 (br s, 2H). LC/MS calcd. for C18H18FN5O2 (m/e) 355.371, obsd. 356.2 (M+H, ES+).

Workup

  1. waitthis solution was stored for 50 days
  2. extractionthe organic compound was extracted into ethyl acetate (3×50 mL)
  3. washThe combined organic extracts were washed with brine solution
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationFiltration and concentration
  6. customgave the crude yellow solid which
  7. customwas purified
  8. washeluting with 0-50% ethyl acetate in hexanes
  9. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-955e94bcc82042028d30d4d9c409bad5
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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