Sodium hydride → HCID 66585065, compound

HRID 2368986Notes

Reaction equation

HRID 2368986 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[O:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[C:23]([NH2:25])[N:22]3[N:26]=[CH:27][C:28]([C:29]4[CH:30]=[N:31][C:32]5[C:37]([CH:38]=4)=[CH:36][CH:35]=[CH:34][CH:33]=5)=[C:21]3[N:20]=2)[CH2:15][CH2:14]1>CN(C=O)C.[NH4+].[Cl-]>[O:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:24]=[C:23]([NH:25][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[N:22]3[N:26]=[CH:27][C:28]([C:29]4[CH:30]=[N:31][C:32]5[C:37]([CH:38]=4)=[CH:36][CH:35]=[CH:34][CH:33]=5)=[C:21]3[N:20]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 256128tert-Butyl 3-bromopropionateHCID 58173399HCID 58173399, compound

Product 1

HCID 66585065HCID 66585065, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

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. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with Na2SO4
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-6898de6c93bc41e88c3f6cc9c19c8c26
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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