Acetic Acid → HCID 5327836, compound

HRID 1602243Notes

Reaction equation

HRID 1602243 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.C(O)(=O)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.[BH3-]C#N.[Na+]>CO.CN1C(=O)N(C)CC1>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][NH:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 5327836HCID 5327836, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

Analogously to Example 21, 1.00 mmol of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol, 13 ml of DMEU and 3.0 mmol of acetic acid are first reacted with 3-chloro-benzaldehyde and then reduced with 7.00 mmol of NaCNBH3 (5-7 days). 3-(3-Chloro-benzylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo-[3,4-d]pyrimidine is obtained; m.p. 158-163° C.; HPLC: TRet (Grad20-100)=12.4.

Sources & evidence

ORD record
ord-ce484708a587446184ef747b32c7de6d
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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