Dimethyl Sulfoxide → HCID 178492630, compound

HRID 1754083Notes

Reaction equation

HRID 1754083 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]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(C)=[O:31]>>[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]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)=[O:31])[N:12]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 178488044HCID 178488044, compound

Product 1

HCID 178492630HCID 178492630, compoundYield 33.4%

Procedure

A light brown solution of 3-(cyclopentylamino)-2-(3,4,5-trimethoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (330 mg, 0.865 mmol) in DMSO (100 mL) was stored for 60 days at RT. Within one day, it became a light brown solution and no precipitation was observed during these 60 days. Then, it was poured into water (1 L) and the resulting precipitate was extracted into EA (2×75 mL). The combined extracts were washed with water, brine solution, and dried over anhydrous MgSO4. Filtration and concentration gave the crude solid which was purified using an ISCO (40 g) column chromatography eluting with 0-70% EA in hexanes. The desired fractions were combined and the solvent was removed under vacuum to obtain 115 mg (33.4%) of (E)-5-amino-1-(1-(cyclopentylimino)-2-(3,4,5-trimethoxyphenyl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile as alight yellow solid. 1H NMR (400 MHz, DMSO-d6): 1.50-1.80 (br m, 8H), 3.67 (p, 1H), 3.79 (s, 3H), 3.81 (s, 6H), 7.06 (s, 2H), 7.7 (s, 1H), 8.12 (br s, 2H). LC/MS calcd. for C20H23N5O4 (m/e) 397.433, obsd. 398.3 (M+H, ES+).

Workup

  1. customno precipitation
  2. waitwas observed during these 60 days
  3. additionThen, it was poured into water (1 L)
  4. extractionthe resulting precipitate was extracted into EA (2×75 mL)
  5. washThe combined extracts were washed with water, brine solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationFiltration and concentration
  8. customgave the crude solid which
  9. customwas purified
  10. washeluting with 0-70% EA in hexanes
  11. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6523afd5dfc74735b91db080d8a3da76
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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