Water → HCID 178486593, compound

HRID 1754077Notes

Reaction equation

HRID 1754077 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[C:26]([O:27][CH3:28])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:29]>CS(C)=O.[Cl-].[Na+].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[C:26]([O:27][CH3:28])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[O:29])[N:12]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

5

Reactant 2

HCID 962WaterHCID 178486592HCID 178486592, compound

Product 1

HCID 178486593HCID 178486593, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A light yellow solution of 3-(cyclopentylamino)-2-(3-methoxynaphthalen-2-yl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (150 mg, 0.404 mmol) in DMSO (6 mL) was stored for 40 days at RT. Then, it was poured into a mixture of water and brine solution (˜150 mL) and the organic compound was extracted into ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave the light yellow oil which was purified using an ISCO (40 g) column chromatography eluting with 0-60% ethyl acetate in hexanes. The desired fractions were combined and the solvent was removed under vacuum to isolate 36 mg (23% yield) of (E)-5-amino-1-(1-(cyclopentylimino)-2-(3-methoxynaphthalen-2-yl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.42-1.64 (br m, 4H), 1.64-1.80 (br, 4H), 3.75 (p, 1H), 3.77 (s, 3H), 7.45 (t, J=2.4 Hz, 1H), 7.48 (s, 1H), 7.64 (s, 1H), 7.65 (t, J=2.4 Hz, 1H) 7.88 (d, 1H), 8.10 (br s, 2H), 8.12 (d, 1H), 8.62 (s, 1H). LC/MS calcd. for C22H21N5O2 (m/e) 387.441, obsd. 388.0 (M+H, ES+).

Workup

  1. extractionthe organic compound was extracted into ethyl acetate (2×50 mL)
  2. washThe combined extracts were washed with brine solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationFiltration and concentration
  5. customgave the light yellow oil which
  6. customwas purified
  7. washeluting with 0-60% ethyl acetate in hexanes
  8. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-26ca41054d214fe5b120346d9f23861c
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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