Triethylamine → HCID 178503366, compound

HRID 1851313Notes

Reaction equation

HRID 1851313 reaction equation
[CH3:1][S:2][C:3]1[N:25]=[C:6]2[N:7]=[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:5]2[N:4]=1.[NH:26]1[CH2:29][CH:28]([C:30]2[NH:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=3)[N:31]=2)[CH2:27]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.CC(O)=O>[CH3:41][C:37]1[N:36]=[C:35]([C:32]2[NH:33][N:34]=[C:30]([CH:28]3[CH2:27][N:26]([CH2:21][C:20]4[CH:23]=[CH:24][C:17]([C:8]5[C:9]([C:11]6[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=6)=[CH:10][N:5]6[N:4]=[C:3]([S:2][CH3:1])[N:25]=[C:6]6[N:7]=5)=[CH:18][CH:19]=4)[CH2:29]3)[N:31]=2)[CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 86703060HCID 86703060, compound

Product 1

HCID 178503366HCID 178503366, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-(2-methylsulfanyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (200 mg, 0.548 mmol), 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (174 mg, 60% pure), triethylamine (0.168 mL), AcOH (0.075 mL) and NMP (4.6 mL) were stirred overnight at room temperature. Sodium triacetoxyborohydride (279 mg) and the mixture stirred for 3 h. The reaction was partitioned between CH2Cl2 and water, the organic phase separated, dried and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (78 mg) as a white solid.

Workup

  1. customThe reaction was partitioned between CH2Cl2 and water
  2. customthe organic phase separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-30b86b7a31ee4b53853dad2174383117
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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