Triethylamine → HCID 178432377, compound

HRID 1915589Notes

Reaction equation

HRID 1915589 reaction equation
C(N(CC)CC)C.Cl.[S:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14]1[NH:18][N:17]=[C:16]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:15]=1.[CH3:25][C:26]1[N:48]=[C:29]2[N:30]=[C:31]([C:40]3[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=3)[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:33][N:28]2[N:27]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.CN(C=O)C.C(O)(=O)C>[CH3:25][C:26]1[N:48]=[C:29]2[N:30]=[C:31]([C:40]3[CH:41]=[CH:42][C:43]([CH2:44][N:22]4[CH2:23][CH2:24][CH:19]([C:16]5[N:15]=[C:14]([C:10]6[S:9][CH:13]=[CH:12][N:11]=6)[NH:18][N:17]=5)[CH2:20][CH2:21]4)=[CH:46][CH:47]=3)[C:32]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:33][N:28]2[N:27]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehydeHCID 178478299HCID 178478299, compound

Product 1

HCID 178432377HCID 178432377, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

0.25 ml triethylamine is added to a solution of 225 mg 4-(5-thiazol-2-yl-1H-[1,2,4]triazol-3-yl)-piperidine hydrochloride in 7.6 ml methanol. To this solution a solution of 250 mg 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (prepared as described under example 37) in 7.6 ml DMF is added, followed by 0.11 ml glacial acetic acid and 337 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Six additional portions of 2 equivalents NaBH(OAc)3 are added over 3 days. The solvent is removed by evaporation and the residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol]) to yield the desired compound.

Workup

  1. customThe solvent is removed by evaporation
  2. customthe residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol])

Sources & evidence

ORD record
ord-d103f2d6e107430e89b37909865616d3
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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