Pyridine-2-carbonitrile → HCID 178420047, compound

HRID 1051316Notes

Reaction equation

HRID 1051316 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:10]3=[N:9][C:8]=2[C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:24]([C:26]([CH:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1)=O)[NH2:25].[N:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[C:47]#[N:48].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(O)(=O)C.N1C=CC=CC=1.C(N(CC)CC)C>[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:10]3=[N:9][C:8]=2[C:16]2[CH:23]=[CH:22][C:19]([CH2:20][N:31]3[CH2:30][CH2:29][CH:28]([C:26]4[N:48]=[C:47]([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=5)[NH:25][N:24]=4)[CH2:33][CH2:32]3)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 5049666Sodium triacetoxyborohydride2×HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 86631773HCID 86631773, compound

Product 1

HCID 178420047HCID 178420047, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

0.14 ml triethylamine is added to a solution of 156 mg 4-(3-phenylimidazo[1,2-a]pyrimidin-2-yl)benzaldehyde in 10 ml methanol. To this solution a solution of 140 mg 2-(5-Piperidin-1,2,4]triazol-3-yl)-pyridine*2HCl (Intermediate A 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) is added, followed by 0.07 ml glacial acetic acid and 198 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Three additional portions of 198 mg NaBH(OAc)3 are added after 2, 4 and 20 hours. The solvents is removed by evaporation after 24 h and the residue purified by chromatography on silica gel (dichlormethan/methanol).

Workup

  1. addition4,011,218 or WO2005100344) is added
  2. customThe solvents is removed by evaporation after 24 h
  3. customthe residue purified by chromatography on silica gel (dichlormethan/methanol)

Sources & evidence

ORD record
ord-16ff37f5c67847afb726b1087136a0aa
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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