Acetic Acid → HCID 178478148, compound

HRID 1068936Notes

Reaction equation

HRID 1068936 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.[NH:23]1[C:27]([C:28]2[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=2[CH:30]=O)=[N:26][N:25]=[N: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:30][C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[C:27]4[NH:23][N:24]=[N:25][N:26]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 178509242HCID 178509242, compoundHCID 178519511HCID 178519511, compound

Product 1

HCID 178478148HCID 178478148, 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 and 343 μl of acetic acid are dissolved in 50 ml of methanol and reacted with 523 mg (3.0 mmol) of 2-(tetrazol-5-yl)-benzaldehyde (Step 61.1) to form 4-(3-chloro-phenylamino)-3{[2-(tetrazol-5-yl)-phenyl]-methyleneamino}-1H-pyrazolo[3,4-d]pyrimidine. The above intermediate is reduced in 30 ml of DMEU with 16 ml (16 mmol) of DIBAL-H and the reaction mixture is hydrolyzed analogously. The DMEU solution is poured into water, adjusted to pH=3 with 1 N HCl and extracted with ethyl acetate. The organic phase yields, after washing 10× with water and 1× with brine, drying (Na2SO4), concentration by evaporation and digestion in diethyl ether, 4-(3-chloro-phenylamino)-3-[2-(tetrazol-5-yl)-benzylamino]-1H-pyrazolo-[3,4-d]pyrimidine; TLC: Rf=0.19 (CHCl3/methanol/H2O/acetic acid=85:13:1.5:0.5); HPLC: tRet(grad20-100)=7.7; FAB-MS: (M+H)+=419.

Sources & evidence

ORD record
ord-d8ee8d18f5f74a34bbc7a85e71f8b577
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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