Methanol → HCID 19610621, compound

HRID 1602235Notes

Reaction equation

HRID 1602235 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][NH:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[NH:11][N:10]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:33]O>>[ClH:25].[Cl:25][C:21]1[CH:20]=[C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[NH:11][N:10]=[C:9]([NH:8][CH2:7][C:6]4[CH:26]=[CH:27][CH:28]=[C:4]([C:1]([O:3][CH3:33])=[O:2])[CH:5]=4)[C:17]=23)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 19610585HCID 19610585, compound

Product 1

HCID 19610621HCID 19610621, compound

Conditions

Temperature
70 °C

Procedure

Preferably, the same compound is obtained as follows: To 70 mg (0.177 mmol) of 3-(3-carboxy-benzyl-amino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (cf. Example 21) and 2 ml of methanol are added 0.1 ml of thionylchloride. The mixture is stirred in a sealed vessel for 3 h at 70° C., and then cooled to room temperature. Filtration and washing with methanol affords 4-(3-chloro-phenylamino)-3-(3-methoxycarbonyl-benzylamino)-1H-pyrazolo[3,4-d]pyrimidine-hydrochloride; (C20H17N6ClO2 ×HCl×0.28H2O), calc. C 53.34, H 4.15, N 18.66, Cl 15.74, H2O 1.12, found C 53.35, H 4.13, N 18.82, Cl 15.87, H2O 1.12.

Workup

  1. customPreferably, the same compound is obtained
  2. temperaturecooled to room temperature
  3. filtrationFiltration
  4. washwashing with methanol

Sources & evidence

ORD record
ord-b75492e09adf49589ff700661a30460e
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

Loading…