Dimethyl Sulfoxide → HCID 178493486, compound

HRID 1754075Notes

Reaction equation

HRID 1754075 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])=[CH:19][C:18]=2[O:27][CH3:28])[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])=[CH:19][C:18]=2[O:27][CH3:28])=[O:31])[N:12]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 178493432HCID 178493432, compound

Product 1

HCID 178493486HCID 178493486, compoundYield 10%

Procedure

A mixture of 3-(cyclopentylamino)-2-(2,4,5-trimethoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (153 mg, 0.401 mmol) and DMSO (20 mL) was heated gently to dissolve all the solids. The resulting brown solution was stored for 30 days at RT. As a result, some solids were precipitated which was collected by filtration and the filtrate was diluted with water (˜100 mL). The resulting solids were collected by filtration and washed with diethyl ether. These solids were again purified by HPLC using acetonitrile and ammonium acetate as eluent to obtain 16.5 mg (10% yield) of (E)-5-amino-1-(1-(cyclopentylimino)-2-(2,4,5-trimethoxyphenyl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.40-1.85 (br m, 8H), 3.65 (s, 3H), 3.67 (p, 1H), 3.79 (s, 3H), 3.91 (s, 3H), 6.72 (s, 1H), 7.35 (s, 1H), 7.63 (s, 1H), 8.06 (br s, 2H). LC/MS calcd. for C20H23N5O4 (m/e) 397.433, obsd. 398.3 (M+H, ES+).

Workup

  1. temperaturewas heated gently
  2. dissolutionto dissolve all the solids
  3. customAs a result, some solids were precipitated which
  4. filtrationwas collected by filtration
  5. additionthe filtrate was diluted with water (˜100 mL)
  6. filtrationThe resulting solids were collected by filtration
  7. washwashed with diethyl ether
  8. customThese solids were again purified by HPLC

Sources & evidence

ORD record
ord-cc07ed3ac6fe48719a837e2b33a79c1c
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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