Dimethylcarbamoyl Chloride → HCID 178484695, compound

HRID 1068943Notes

Reaction equation

HRID 1068943 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].O.[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:25]3[C:20](=[N:21][CH:22]=[N:23][C:24]=3[NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[NH:19][N:18]=2)=[CH:12][CH:11]=1.C(N(CC)CC)C>C1COCC1>[Cl:33][C:29]1[CH:28]=[C:27]([NH:26][C:24]2[N:23]=[CH:22][N:21]=[C:20]3[NH:19][N:18]=[C:17]([NH:16][C:13]4[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:3]([N:2]([CH3:6])[CH3:1])=[O:4])=[CH:11][CH:12]=4)[C:25]=23)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178510043HCID 178510043, compound

Product 1

HCID 178484695HCID 178484695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.0503 ml (0.548 mmol) of dimethylcarbamoyl chloride in 0.5 ml of THF is added dropwise, with stirring, to a suspension, cooled to 0° C., of 150 mg (0.391 mmol) of 3-(4-aminomethyl-phenylamino)4-(3-chloro-phenylamino)-1H-pyrazolo-[3,4-d]pyrimidine hydrate (see Step 77.5) in 2.5 ml of THF and 0.079 ml (0.567 mmol) of triethylamine. The reaction mixture is stirred at RT for 17 hours and then filtered, and the filter residue is washed in succession with THF, water, THF and diethyl ether. 4-(3-Chloro-phenylamino)-3-[4-(dimethylamino-carbonylamino-methyl)-phenylamino]-1H-pyrazolo[3,4-d]pyrimidine having a water content of 1.22% is obtained; m.p. 238-240° C.; ESI-MS: (M+H)+=437.

Workup

  1. stirringThe reaction mixture is stirred at RT for 17 hours
  2. filtrationfiltered
  3. washthe filter residue is washed in succession with THF, water, THF and diethyl ether

Sources & evidence

ORD record
ord-66e906e7f5424ef2892455541524a9dd
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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