Acetic Acid → HCID 178514086, compound

HRID 1068944Notes

Reaction equation

HRID 1068944 reaction equation
O.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[NH:13][N:12]=2)=[CH:6][CH:5]=1.[O-:28][C:29]#[N:30].[K+].C(O)C.C(O)(=O)C>O>[Cl:27][C:23]1[CH:22]=[C:21]([NH:20][C:18]2[N:17]=[CH:16][N:15]=[C:14]3[NH:13][N:12]=[C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([CH2:3][NH:2][C:29]([NH2:30])=[O:28])=[CH:5][CH:6]=4)[C:19]=23)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 11378442Potassium cyanateHCID 178510043HCID 178510043, compound

Product 1

HCID 178514086HCID 178514086, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 150 mg (0.391 mmol) of 3-(4-aminomethyl-phenylamino)-4-(3chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine hydrate (see Step 77.5), 95 mg (1.17 mmol) of potassium cyanate, 3 ml of ethanol, 3 ml of water and 0.0258 ml (0.451 mmol) of acetic acid is heated under reflux for 1 hour. After cooling to about 20° C., filtration and recrystallization of the filtration residue from methanol/water, 4-(3-chloro-phenylamino)-3-(4-{ureido-methyl}-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine is obtained; m.p. >280° C.; FAB-MS: (M+H)+=409.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. filtrationfiltration and recrystallization of the filtration residue from methanol/water

Sources & evidence

ORD record
ord-7fd16b0d29504e5cbd618fbaffe2b66c
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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