Acetic Acid → HCID 178481994, compound

HRID 1068918Notes

Reaction equation

HRID 1068918 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.[CH3:23][N:24]1[N:28]=[N:27][C:26]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[CH:32]=O)=[N:25]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:34]=[CH:35][CH:36]=[C:29]([C:26]5[N:27]=[N:28][N:24]([CH3:23])[N:25]=5)[CH:30]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10750107HCID 10750107, compoundHCID 178509242HCID 178509242, compound

Product 1

HCID 178481994HCID 178481994, 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 565 mg (3.0 mmol) of 3-(2-methyl-tetrazol-5-yl)-benzaldehyde to form 4-(3-chloro-phenylamino)-3-[{3-(2-methyl-tetrazol-5-yl)-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 methanol yield 4-(3-chloro-phenylamino)-3-[3-(2-methyl-tetrazol-5-yl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine; TLC: Rf=0.51 (CHCl3/methanol/H2O/acetic acid=85:13:1.5:0.5); HPLC: tRet(grad20-100)=8.7; FAB-MS: (M+H)+=433.

Sources & evidence

ORD record
ord-6100284bcbaf458f93182c28b3f8f0fb
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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