Triethylamine → HCID 178437215, compound

HRID 1851290Notes

Reaction equation

HRID 1851290 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)=[N:8][C:7]=12)[CH3:2].Cl.[NH:27]1[CH2:30][CH:29]([C:31]2[N:32]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[N:37]=3)[NH:34][N:35]=2)[CH2:28]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[CH2:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:18]3[CH:25]=[CH:24][C:21]([CH2:22][N:27]4[CH2:28][CH:29]([C:31]5[N:32]=[C:33]([C:36]6[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[N:37]=6)[NH:34][N:35]=5)[CH2:30]4)=[CH:20][CH:19]=3)=[N:8][C:7]=12)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86630679HCID 86630679, compoundHCID 178424643HCID 178424643, compound

Product 1

HCID 178437215HCID 178437215, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 142 mg (0.43 mmol) 4-(3-ethyl-6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzaldehyde and 314 mg (0.65 mmol, ca 60% pure) 2-(5-azetidin-3-yl-2H-[1,2,4]triazol-3-yl)-6-methyl-pyridine hydrochloride salt in 3.65 mL NMP was treated with 0.146 mL triethylamine and 0.045 mL acetic acid and stirred overnight at rt. The mixture was treated with 101 mg sodium triacetoxyborohydride and stirred overnight at rt. The reaction was partitioned between DCM and saturated sodium hydrogencarbonate solution, the organic phase dried and concentrated in vacuo and the residue purified by preparative reverse phase HPLC to give 49 mg of the title compound contaminated with formic acid.

Workup

  1. stirringstirred overnight at rt
  2. customThe reaction was partitioned between DCM and saturated sodium hydrogencarbonate solution
  3. customthe organic phase dried
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-6b6102f8330b47909f05e5ba5948bfe0
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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