Pyridine-2-carbonitrile → HCID 178524057, compound

HRID 503811Notes

Reaction equation

HRID 503811 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-5bac793831f9403297d30a9a0e35c22f
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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