Water → HCID 178510463, compound

HRID 1754069Notes

Reaction equation

HRID 1754069 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[N:11]([C:17]=2[NH:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[N:12]=[CH:13][C:14]=3[C:15]#[N:16])=[CH:4][CH:3]=1.[OH2:24]>CS(C)=O.ClCCl>[NH2:9][C:10]1[N:11](/[C:17](=[N:18]/[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)/[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[O:24])[N:12]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

5

Reactant 2

HCID 962WaterHCID 178510453HCID 178510453, compound

Product 1

HCID 178510463HCID 178510463, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A dilute solution of 2-(4-bromophenyl)-3-(cyclopentylamino)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (500 mg, 1.35 mmol) in DMSO (100 mL) was stored at RT for more than 60 days. The yellow DMSO solution was poured into water (1 L) and the organic compound was extracted into ethyl acetate (2×75 mL). The combined extracts were washed with water and brine solution. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give the crude yellow solid which was not soluble in dichloromethane even at hot condition. Then, after cooling to RT, the solids were collected by filtration and washed with dichloromethane and the 1H NMR of this solid indicated that it is mostly starting material. Whereas, the mother liquor was removed under vacuum and the crude residue was purified using an ISCO (80 g) column eluting with 0-35% ethyl acetate in hexanes. The pure fractions were combined and the solvent was removed under vacuum to obtain 113 mg (21.7% yield) of (E)-5-amino-1-(1-(cyclopentylimino)-2-(4-bromophenyl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.40-1.80 (br m, 8H), 3.63 (p, 1H), 7.72 (s, 1H), 7.78 (d, J=6.1 Hz, 2H), 7.83 (d, J=6.2 Hz, 2H), 8.14 (br s, 2H). LC/MS calcd. for C17H16BrN5O (m/e) 386.25, obsd. 387.2 (M+H, ES+).

Workup

  1. extractionthe organic compound was extracted into ethyl acetate (2×75 mL)
  2. washThe combined extracts were washed with water and brine solution
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude yellow solid which
  7. filtrationthe solids were collected by filtration
  8. washwashed with dichloromethane
  9. customWhereas, the mother liquor was removed under vacuum
  10. customthe crude residue was purified
  11. washeluting with 0-35% ethyl acetate in hexanes
  12. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2cd77c234d6b48f2a00654ad758e6785
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

Loading…