Propionyl chloride → HCID 57717530, compound

HRID 1984463Notes

Reaction equation

[NH2:1][C:2]([CH3:23])([CH3:22])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][O:20][CH3:21])[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:24](Cl)(=[O:27])[CH2:25][CH3:26]>>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH2:19][O:20][CH3:21])[C:4]([CH2:3][C:2]([NH:1][C:24](=[O:27])[CH2:25][CH3:26])([CH3:23])[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 57717558HCID 57717558, compound

Product 1

HCID 57717530HCID 57717530, compoundYield 73.4%

Procedure

Using the general method of Example 599, 1-(2-amino-2-methylpropyl)-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (500 mg, 1.60 mmol, prepared as described in Example 590) was reacted with propionyl chloride (370 mg, 4.00 mmol). The crude product was purified by IFC (silica gel eluting with a gradient of 15 to 50% CMA in chloroform) followed by recrystallization from ethyl acetate/hexanes to provide 434 mg of N-{2-[4-amino-2-(methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-1,1-dimethylethyl}propionamide as a white solid, mp 157-158° C. MS (APCI) m/z 370 (M+H)+; Anal. Calcd for C20H27N5O2: C, 65.02; H, 7.37; N, 18.96. Found: C, 64.79; H, 7.58; N, 18.94.

Workup

customThe crude product was purified by IFC (silica gel eluting with a gradient of 15 to 50% CMA in chloroform)
customfollowed by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-abb4c0406f4d490eaf2a6873c3bbb2c9
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544697B2

Reaction notes

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