Dimethylformamide → HCID 44467612, compound

HRID 2046966Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[N:4][C:5]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][N:14]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:15]3=[O:18])=[CH:11][C:10]=2[O:25][CH:26]([CH3:28])[CH3:27])=[N:6][CH:7]=1.[CH2:42]([N:44]([CH2:47]C)[CH2:45]C)[CH3:43].CN(C=[O:53])C>>[Cl:1][C:2]1[C:3]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[N:4][C:5]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][N:14]([CH:19]4[CH2:20][CH2:21][N:22]([C:43](=[O:53])[CH2:42][N:44]([CH3:47])[CH3:45])[CH2:23][CH2:24]4)[C:15]3=[O:18])=[CH:11][C:10]=2[O:25][CH:26]([CH3:28])[CH3:27])=[N:6][CH:7]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 248164386-(5-Chloro-4-(2-(isopropylsulfonyl)phenylamino)-pyrimidin-2-ylamino)-5-isopropoxy-2-(piperidin-4-yl)isoindolin-1-one

Product 1

HCID 44467612HCID 44467612, compound

Procedure

To a solution of 6-(5-chloro-4-(2-(isopropylsulfonyl)phenylamino)-pyrimidin-2-ylamino)-5-isopropoxy-2-(piperidin-4-yl)isoindolin-1-one (20 mg, 0.03 mmol) in DMF (1.0 mL) was added 2-(dimethylamion)acetyl chloride hydrochloride (0.17 mmol, 26 mg) and triethyl amine (0.18 mmol, 18 mg). The reaction mixture was stirred at room temperature 1 h and the solid byproduct was removed by filtration. The remaining filtrate was purified by preparative RP-HPLC to afford 6-(5-chloro-4-(2-(isopropylsulfonyl)-phenylamino)pyrimidin-2-ylamino)-2-(1-(2-(dimethylamino)acetyl)piperidin-4-yl)-5-isopropoxyisoindolin-1-one.

Workup

customthe solid byproduct was removed by filtration
customThe remaining filtrate was purified by preparative RP-HPLC

Sources & evidence

ORD record: ord-d676c174806d45668626e00129d22fc6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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