Acetic Acid → HCID 178478146, compound

HRID 1068916Notes

Reaction equation

HRID 1068916 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.[S:23]1[C:27]([C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)=[CH:26][N:25]=[CH:24]1>CO>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][N:3]=[C:2]([N:1]=[CH:32][C:31]4[CH:30]=[CH:29][C:28]([C:27]5[S:23][CH:24]=[N:25][CH:26]=5)=[CH:35][CH:34]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10774002HCID 10774002, compoundHCID 178509242HCID 178509242, compound

Product 1

HCID 178478146HCID 178478146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to Example 32, 521 mg (2.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6) and 343 μl of acetic acid are dissolved in 50 ml of methanol and reacted with 567 mg (3.0 mmol) of 4-(thiazol-5-yl)-benzaldehyde to form 4-(3-chloro-phenylamino)-3-[{4-(thiazol-5yl)-phenyl}-methyleneamino]-1H-pyrazolo[3,4-d]pyrimidine. Reduction of the above intermediate in 30 ml of DMEU with 16 ml (16 mmol) of DIBAL-H, analogous working-up and digestion in diethyl ether yield 4-(3-chloro-phenylamino)-3-[4-(thiazol-5-yl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine; m.p. 235° C.; TLC: Rf=0.42 (CHCl3/methanol/H2O/acetic acid=85:13:1.5:0.5); HPLC: tRet(grad20-100)=8.5; FABMS: (M+H)+=434.

Sources & evidence

ORD record
ord-22c632a5eb7e4049add39d424577e331
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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