Succinic anhydride → HCID 178511410, compound

HRID 1068942Notes

Reaction equation

HRID 1068942 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.O.[NH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:26]3[C:21](=[N:22][CH:23]=[N:24][C:25]=3[NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)[NH:20][N:19]=2)=[CH:13][CH:12]=1>C1COCC1>[C:1]([CH2:2][CH2:3][C:4]([CH:10]([NH2:9])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:26]3[C:21](=[N:22][CH:23]=[N:24][C:25]=3[NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)[NH:20][N:19]=2)=[CH:13][CH:12]=1)=[O:5])([OH:6])=[O:7]

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 178510043HCID 178510043, compound

Product 1

HCID 178511410HCID 178511410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 57.4 mg (0.573 mmol) of succinic anhydride in 0.5 ml of THF is added dropwise, with stirring, to a suspension, cooled to 0° C., of 200 mg (0.521 mmol) of 3-(4-aminomethyl-phenylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine hydrate (see Step 77.5) in 3 ml of THF. The reaction mixture is stirred at RT for 4 hours and then a further solution of 57.4 mg (0.573 mmol) of succinic anhydride in 0.5 ml of THF is added. The mixture is stirred for a further 3 hours at 40° C., then allowed to cool to RT and filtered, and the filter residue is washed with diethyl ether. 3-[4-({3-Carboxy-propionyl}-aminomethyl)-phenylamino]-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine having a water content of 2.45% is obtained; m.p. 205-207° C.; ESI-MS: (M−H)−=464.

Workup

  1. stirringThe reaction mixture is stirred at RT for 4 hours
  2. stirringThe mixture is stirred for a further 3 hours at 40° C.
  3. filtrationfiltered
  4. washthe filter residue is washed with diethyl ether

Sources & evidence

ORD record
ord-05366e117a2d4f018485955329abd020
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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