Triethylamine → HCID 136128346, compound

HRID 220900Notes

Reaction equation

HRID 220900 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.Cl.[CH3:9][N:10]1[C:19]2[NH:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[N:15]([C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[C:28]([CH3:42])[CH:27]=3)=[O:25])[CH2:14][C:13]=2[CH:12]=[N:11]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.ClCCl.C(O)(=O)C>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][N:39]1[CH2:40][CH2:41][CH:36]([CH2:35][CH2:34][CH2:33][O:32][C:29]2[CH:30]=[CH:31][C:26]([C:24]([N:15]3[CH2:14][C:13]4[CH:12]=[N:11][N:10]([CH3:9])[C:19]=4[NH:18][C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]3=4)=[O:25])=[CH:27][C:28]=2[CH3:42])[CH2:37][CH2:38]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 763353,3-DimethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 136346641(3-Methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-[3-methyl-4-(3-piperidin-4-yl-propoxy)-phenyl]-methanone Hydrochloride

Product 1

HCID 136128346HCID 136128346, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (0.05 ml) and 3,3-dimethylbutyraldehyde (0.024 ml, 0.19 mmol) were added to a solution of (3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-[3-methyl-4-(3-piperidin-4-yl-propoxy)-phenyl]-methanone hydrochloride from Example E68.5 (60 mg, 0.12 mmol) in methanol (2.45 ml) and triethylamine (0.026 ml, 0.19 mmol). The mixture was stirred at room temperature for 1 h then sodium triacetoxyborohydride (40 mg, 0.19 mmol) was added. The mixture was stirred at room temperature for 18 h, diluted with dichloromethane, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white fluffy solid identified as the title compound (33 mg, 48%).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. washwashed with saturated NaHCO3
  3. dry with materialbrine, dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  6. customto give a white fluffy solid

Sources & evidence

ORD record
ord-5e7d346c19f84e53b06aaf8e9e5fec88
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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