Acetic Acid → HCID 178478153, compound

HRID 1068897Notes

Reaction equation

HRID 1068897 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.[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH: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:29][C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 178509242HCID 178509242, compound

Product 1

HCID 178478153HCID 178478153, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to Step 32.1, 261 mg (1.00 mmol) of 3-amino-4-(3-chloro-phenyl-amino)-1 H-pyrazolo[3,4-d]pyrimidine (see Step 1.6) and 180 mg of acetic acid are dissolved in 26 ml of methanol and reacted with 161 mg (1.5 mmol) of pyridine-4-carbaldehyde to form 4-(3-chloro-phenylamino)-3-[(pyrid-4-yl)-methyleneamino]-1H-pyrazolo[3,4-d]pyrimidine. Reduction of the above intermediate in 25 ml of DMEU with 8 ml (8 mmol) of DIBAL-H analogously to Example 32 and analogous working-up yield 4-(3-chlorophenylamino)-3-[(pyrid-4-yl)-methylamino]-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)7.7; FAB-MS: (M+H)+=352.

Sources & evidence

ORD record
ord-35f763a37254447abdfcc29b64dbeda2
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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