Acetic Acid → HCID 178448767, compound

HRID 1068921Notes

Reaction equation

HRID 1068921 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.[C:23]([N:27]1[N:31]=[N:30][C:29]([C:32]2[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=2)[CH:35]=O)=[N:28]1)([CH3:26])([CH3:25])[CH3:24]>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:35][C:34]4[CH:37]=[CH:38][CH:39]=[C:32]([C:29]5[N:30]=[N:31][N:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:28]=5)[CH:33]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21190634HCID 21190634, compoundHCID 178509242HCID 178509242, compound

Product 1

HCID 178448767HCID 178448767, 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 691 mg (3.0 mmol) of 3-(2-tert-butyl-tetrazol-5-yl)-benzaldehyde to form 4-(3-chloro-phenylamino)-3-[{3-(2-tert-butyl-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-tert-butyl-tetrazol-5-yl)-benzylamino]1H-pyrazolo[3,4-d]pyrimidine; TLC: Rf=0.60 (CHCl3/methanol/H2O/acetic acid=85:13:1.5:0.5); HPLC: tRet(grad20-100)=10.3.

Sources & evidence

ORD record
ord-00314e0ca70b45c5be9c67b4f796aa24
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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