Triethylamine → HCID 57555278, compound

HRID 220905Notes

Reaction equation

HRID 220905 reaction equation
Cl.Cl.[CH2:3]([N:10]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]([C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[C:28]([CH3:42])[CH:27]=3)=[O:25])[CH2:15][CH2:14][C:13]=2[N:12]=[C:11]1[CH3:43])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:51][C:52]([CH3:57])([CH3:56])[CH2:53][CH:54]=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH2:3]([N:10]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]([C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][N:39]([CH2:54][CH2:53][C:52]([CH3:57])([CH3:56])[CH3:51])[CH2:38][CH2:37]4)=[C:28]([CH3:42])[CH:27]=3)=[O:25])[CH2:15][CH2:14][C:13]=2[N:12]=[C:11]1[CH3:43])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 67286922HCID 67286922, compound

Product 1

HCID 57555278HCID 57555278, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

(1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-[3-methyl-4-(3-piperazin-1-yl-propoxy)-phenyl]-methanone dihydrochloride from Example E70.2 (100 mg, 0.16 mmol) was dissolved in methanol (2.45 ml) and triethylamine (0.068 ml, 0.48 mmol). Acetic acid (0.05 ml) then 3,3-dimethylbutyraldehyde (0.031 ml, 0.24 mmol) were added and the mixture was stirred for 1 h at room temperature. Sodium cyanoborohydride (16 mg, 0.24 mmol) was added and the mixture was stirred for 20 h at room temperature then concentrated in vacuo. The residue was dissolved in dichloromethane, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo to yield the title compound (98 mg, 96%).

Workup

  1. stirringthe mixture was stirred for 20 h at room temperature
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2b96922fbd9428e9fb3c0b8eaefd7d5
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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