Propionyl chloride → HCID 57717530, compound

HRID 1360539Notes

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-4778a3e23d314b28bddfab4b3418ff2c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879849B2

Reaction notes

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