Pyridine-2-carbonitrile → HCID 178524057, compound

HRID 1915616Notes

Reaction equation

HRID 1915616 reaction equation
N(C(C1CCN(C(OC(C)(C)C)=O)CC1)=[O:4])N.N1C=CC=CC=1C#N.[C:26]1([C:32]2[C:33]([C:44]3[CH:49]=[CH:48][C:47]([CH2:50][N:51]4[CH2:56][CH2:55][CH:54]([C:57]5[N:61]=[C:60]([C:62]6[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=6)[NH:59][N:58]=5)[CH2:53][CH2:52]4)=[CH:46][CH:45]=3)=[N:34][C:35]3[N:36]([N:38]=[C:39]([C:41](N)=[O:42])[CH:40]=3)[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.CN(C=O)C.C(O)(=O)C.C(N(CC)CC)C>[C:26]1([C:32]2[C:33]([C:44]3[CH:45]=[CH:46][C:47]([CH2:50][N:51]4[CH2:52][CH2:53][CH:54]([C:57]5[N:61]=[C:60]([C:62]6[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=6)[NH:59][N:58]=5)[CH2:55][CH2:56]4)=[CH:48][CH:49]=3)=[N:34][C:35]3[N:36]([N:38]=[C:39]([C:41]([OH:42])=[O:4])[CH:40]=3)[CH:37]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 178513501HCID 178513501, compound

Product 1

HCID 178524057HCID 178524057, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.14 ml triethylamine are added to a solution of 101 mg 2-(5-piperidin-4H[1,2,4]triazol-3-yl)-pyridine*2HCl (prepared from tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate and pyridine-2-carbonitrile according to a procedure described in U.S. Pat. No. 4,011,218 or WO2005100344) in 5 ml methanol. To this solution a solution of 150 mg 5-(4-formylphenyl)-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid (prepared as described under example 78) in 15 ml DMF is added, followed by 0.07 ml glacial acetic acid and 186 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1, 2 and 3 hours. The solvent is removed by evaporation after 20 h and the residue is purified by RP HPLC (water, 10 mM NH4COOH, pH 3.7/ACN) to yield the desired compound.

Workup

  1. customThe solvent is removed by evaporation after 20 h
  2. customthe residue is purified by RP HPLC (water, 10 mM NH4COOH, pH 3.7/ACN)

Sources & evidence

ORD record
ord-c233d46bbef54feb8dd295aa6f97e9cf
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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