Hydrochloric Acid → HCID 66584647, compound

HRID 2368987Notes

Reaction equation

HRID 2368987 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[N:10]3[N:23]=[CH:24][C:25]([C:26]4[CH:27]=[N:28][C:29]5[C:34]([CH:35]=4)=[CH:33][CH:32]=[CH:31][CH:30]=5)=[C:9]3[N:8]=2)[CH2:3][CH2:2]1.Cl>O1CCOCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[C:11]([NH:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[N:10]3[N:23]=[CH:24][C:25]([C:26]4[CH:27]=[N:28][C:29]5[C:34]([CH:35]=4)=[CH:33][CH:32]=[CH:31][CH:30]=5)=[C:9]3[N:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66585065HCID 66585065, compound

Product 1

HCID 66584647HCID 66584647, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

NaH (25.1 mg, 60%, 0.63 mmol) and then tert-butyl 3-bromopropanoate (69.7 uL, 0.42 mmoL) was added to 5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (72.3 mg, 0.21 mmoL) in DMF (3 mL). The mixture was stirred at room temperature until LCMS indicated complete conversion. The reaction mixture was diluted with Sat. NH4Cl and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation of solvent afforded the crude tert-butyl 3-(5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-ylamino)propanoate. The crude ester was heated with 4N HCl (4 mL) and 1,4-dioxane (4 mL) at 50° C. for 3 h. Concentration provided 3-(5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-ylamino)propanoic acid. LCMS tR=1.10 Min (5 min run, UV254nm). Mass calculated for, M+ 418.1, observed LC/MS m/z 419.2 (M+H).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-024263ea0eaf4f47bc686fb796587562
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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