Dimethyl Sulfoxide → HCID 178492928, compound

HRID 1754071Notes

Reaction equation

HRID 1754071 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]([F:23])=[CH:19][C:18]=2[O:24][CH3:25])[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(C)=[O:28]>>[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]([F:23])=[CH:19][C:18]=2[O:24][CH3:25])=[O:28])[N:12]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 178492923HCID 178492923, compound

Product 1

HCID 178492928HCID 178492928, compoundYield 35%

Procedure

A light yellow solution of 3-(cyclopentylamino)-2-(4-fluoro-2-methoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (130 mg, 0.383 mmol) in DMSO (5 mL) was kept at RT in a 10 mL vial. The resulting light yellow solution was stored for 60 days. Then, the crude compound in DMSO was purified by using an HPLC column chromatography using acetonitrile and ammonium acetate as eluent. The desired peak was collected and the solvent was removed under vacuum to obtain 48 mg (35% yield) of (E)-5-Amino-1-(1-(cyclopentylimino)-2-(4-fluoro-2-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.40-1.62 (br m, 4H), 1.62-1.78 (br, 4H), 3.67 (p, 1H), 3.70 (s, 3H), 7.01 (dt, 1H), 7.13 (dd, 1H), 7.66 (s, 1H), 7.99 (dd, 1H), 8.06 (brvs, 2H). LC/MS calcd. for C18H18FN5O2 (m/e) 355.371, obsd. 355.9 (M+H, ES+).

Workup

  1. customwas kept at RT in a 10 mL
  2. customThen, the crude compound in DMSO was purified
  3. customThe desired peak was collected
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-492e66680ad7431eb7ca43f89e072a44
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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