Dimethylcarbamoyl Chloride → HCID 57899364, compound

HRID 1024604Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[NH:15][N:16]=[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([B:30]3[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]3)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>N1C=CC=CC=1.O>[CH3:39][N:40]([CH3:44])[C:41]([N:15]1[C:12]2[C:13](=[O:14])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9]([C:24]3[CH:29]=[CH:28][C:27]([B:30]4[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]4)=[CH:26][CH:25]=3)=[N:10][C:11]=2[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:16]1)=[O:42]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(4-chloro-phenyl)-3-phenyl-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one (100.0 mg, 0.191 mmol) in anhydrous pyridine (1.0 mL) is added dimethylcarbamyl chloride (87.4 μL, 0.953 mmol). The reaction mixture is heated at 80° C. overnight before removal of the solvent. The residue is taken in water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layer is washed with brine, concentrated, and purified by silica gel chromatography to provide 6-(4-chloro-phenyl)-7-oxo-3-phenyl-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-6,7-dihydro-pyrazolo[4,3-d]pyrimidine-1-carboxylic acid dimethylamide as a white solid product; HPLC-MS calculated for C32H31BClN5O4 (M+H+) 596.2, found 596.2.

Workup

extractionextracted with EtOAc (3×10 mL)
washThe combined organic layer is washed with brine
concentrationconcentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-9e63a13f6c0d48288cf5a96811b2348f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722691B2

Reaction notes

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