Ethyl Acetate → HCID 10277152, compound

HRID 1796558Notes

Reaction equation

HRID 1796558 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[N:15][N:16]4[C:21](Cl)=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=O)C.[CH:38]1([NH2:41])[CH2:40][CH2:39]1>>[Cl:23][C:19]1[CH:20]=[C:21]([NH:41][CH:38]2[CH2:40][CH2:39]2)[N:16]2[N:15]=[C:14]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[N:12]=3)=[C:17]2[CH:18]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 69828CyclopropylamineHCID 10297860HCID 10297860, compound

Product 1

HCID 10277152HCID 10277152, compoundYield 71%

Procedure

N-Cyclopentyl-4-[5,7-dichloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (271 mg, 0.60 mmol) in cyclopropylamine (5 mL) was heated at 100° C. for 11 hours in a steel bomb. Cooled to room temperature. Ethyl acetate was added to the reaction mixture. The solution was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by purification with flash chromatography (4:1 hexanes/ethyl acetate) gave N-{4-[5-chloro-7-(cyclopropylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopentylamine (201 mg, yield 71%) as a yellow foam. 1H NMR (CDCl3) δ 8.02 (d, 1H), 7.96 (s, 1H), 7.56 (d, 2H), 7.01 (d, 2H), 6.42 (s, 1H), 6.37 (d, 1H), 6.32 (d, 1H), 5.12 (d, 1H), 4.15 (m, 1H), 3.91 (s, 3H), 2.70 (m, 1H), 2.08 (m, 2H), 1.82–1.59 (m, 6H), 0.95 (m, 2H), 0.80 (m, 2H); MS m/z 475 (M+1).

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customfollowed by purification with flash chromatography (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-108e8284b1c4438b89cb5720641581e6
Source dataset
uspto-grants-2006_04
Patent number
US07030134B2

Reaction notes

Loading…