Propionyl chloride → HCID 57717542, compound

HRID 1984462Notes

Reaction equation

[NH2:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][CH3:20])[N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17].[C:23](Cl)(=[O:26])[CH2:24][CH3:25]>>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH2:19][CH3:20])[C:4]([CH2:3][C:2]([NH:1][C:23](=[O:26])[CH2:24][CH3:25])([CH3:21])[CH3:22])=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

Reactant 2

HCID 62324Propionyl chloride

HCID 57717565HCID 57717565, compound

Product 1

HCID 57717542HCID 57717542, compoundYield 77.1%

Procedure

Using the method of Example 68, 1-(2-amino-2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 64, 595 mg, 2.00 mmol) was reacted with propionyl chloride (463 mg, 5.00 mmol). The crude product was purified by IFC (silica gel eluting with a gradient of 15 to 25% CMA in chloroform) followed by recrystallization from ethyl acetate/hexanes to provide 545 mg of N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]propionamide as a white solid, mp 158-159° C. MS (APCI) m/z 354 (M+H)+; Anal. Calcd for C20H27N5O: C, 67.96; H, 7.70; N, 19.81. Found: C, 67.80; H, 8.08; N, 19.77

Workup

customThe crude product was purified by IFC (silica gel eluting with a gradient of 15 to 25% CMA in chloroform)
customfollowed by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-372aa7a893ff40ac8846edfc922b36a3
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544697B2

Reaction notes

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