Ethyl Acetate → HCID 10140340, compound

HRID 1062881Notes

Reaction equation

HRID 1062881 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]2[N:14]=[C:15]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](S(C)=O)[N:18]=3)=[C:4]2[CH:3]=1.C(OCC)(=O)C.[CH:40]1([NH2:43])[CH2:42][CH2:41]1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]2[N:14]=[C:15]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:43][CH:40]4[CH2:42][CH2:41]4)[N:18]=3)=[C:4]2[CH:3]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 69828CyclopropylamineHCID 10184433HCID 10184433, compound

Product 1

HCID 10140340HCID 10140340, compoundYield 83%

Procedure

A solution of N-{5-chloro-2-(4-methoxyphenyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-yl}-N-cyclopentylamine (118 mg, 0.24 mmol) in cyclopropylamine (5 mL) was heated at 45° C. in a sealed tube for 5 hours. The reaction mixture was cooled to room temperature and ethyl acetate was added to the reaction mixture. The organic phase was washed with water, brine and dried over magnesium sulfate. Filtration and concentration followed by chromatography (7:3 hexanes:ethyl acetate) gave N-{4-[5-chloro-7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopropylamine (96 mg, 83%) as a yellow solid. 1H NMR (CDCl3) δ 8.10 (broad s, 1H), 8.00 (d, 1H), 7.55 (d, 2H), 6.98 (d, 2H), 6.33 (d, 1H), 6.09 (d, 1H), 5.98 (d, 1H), 5.68 (s, 1H), 3.93 (m, 1H), 3.86 (s, 3H), 2.84 (m, 1H), 2.10 (m, 2H), 1.78-1.65 (m, 6H), 0.90 (m, 2H), 0.63 (m, 2H). MS m/z 475 (M+1).

Workup

  1. washThe organic phase was washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ba152a4cf3d24d058f15826bdc868c53
Source dataset
uspto-grants-2005_11
Patent number
US06962914B2

Reaction notes

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