Methyl isothiocyanate → HCID 178486107, compound

HRID 1068941Notes

Reaction equation

HRID 1068941 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.[CH3:28][N:29]=[C:30]=[S:31]>C1COCC1>[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:30]([NH:29][CH3:28])=[S:31])=[CH:5][CH:6]=4)[C:19]=23)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 178510043HCID 178510043, compound

Product 1

HCID 178486107HCID 178486107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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), 31.4 mg (0.429 mmol) of methyl isothiocyanate and 5 ml of THF is stirred at 20° C. for 15 hours. Concentration to a volume of about 1 ml, addition of 5 ml of diethyl ether to the concentrate and filtration yield 4-(3-chloro-phenylamino)-3-[4-(methylamino-thiocarbonylamino-methyl)phenylamino]-1H-pyrazolo[3,4-d]pyrimidine having a water content of 1.22%; m.p. 216-218° C. (decomp.), ESI-MS: (M−H)−=437.

Workup

  1. concentrationConcentration
  2. additionto a volume of about 1 ml, addition of 5 ml of diethyl ether to the
  3. concentrationconcentrate
  4. filtrationfiltration

Sources & evidence

ORD record
ord-cb901b7de9974e729428e11f11f258db
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

Loading…