3-Amino-1-propanol → 3-[[4-[7-(Butylamino)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl]amino]propan-1-ol

HRID 1373815Notes

Reaction equation

HRID 1373815 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](S(C)=O)[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:31][CH2:32][CH2:33][CH2:34][OH:35]>O1CCCC1>[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:31][CH2:32][CH2:33][CH2:34][OH:35])[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 10295871HCID 10295871, compound

Product 1

HCID 52756933-[[4-[7-(Butylamino)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl]amino]propan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (50 mg, 0.12 mmol) and 3-amino-1-propanol (0.45 mL, 5.9 mmol) in 2 mL tetrahydrofuran was heated to reflux for 4 hours, then the mixture was cooled to room temperature and concentrated. Flash column chromatography eluting with a gradient of 0% to 100% ethyl acetate in hexanes afforded 3-({4-[7-(butylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinyl}amino)-1-propanol (46.3 mg, 90%) as a yellow foam. 1H NMR (CDCl3): δ 7.97 (d, 1H), 7.67–7.61 (m, 3H), 7.35 (t, 1H), 7.16 (t, 2H), 6.34 (d, 1H), 6.04 (m, 2H), 3.67–3.60 (m, 4H), 3.39 (q, 2H), 1.79–1.45 (m, 6H), 1.00 (t, 3H); 19F NMR (CDCl3): δ −113.10; MS m/z 435 (M+1).

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationconcentrated
  3. washFlash column chromatography eluting with a gradient of 0% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-30a48ac522a844f8a039e83c81f69d3f
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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