Sodium Bicarbonate → HCID 23152803, compound

HRID 1012323Notes

Reaction equation

HRID 1012323 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][C:30]([C:33]4[NH:34][C:35]5[CH:41]=[C:40]([C:42]([OH:44])=O)[CH:39]=[CH:38][C:36]=5[N:37]=4)([CH3:32])[CH3:31])=[O:28])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:45][NH:46][CH3:47].O1CCCC1.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.O.CO>[CH3:45][N:46]([CH3:47])[C:42]([C:40]1[CH:39]=[CH:38][C:36]2[N:37]=[C:33]([C:30]([NH:29][C:27]([C:24]3[CH:25]=[CH:26][C:8]4[C:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[C:16]5[N:10]([CH2:11][CH2:12][O:13][C:14]6[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:15]=65)[C:9]=4[CH:23]=3)=[O:28])([CH3:32])[CH3:31])[NH:34][C:35]=2[CH:41]=1)=[O:44]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 22320367Dimethylamine tetrahydrofuranHCID 23152337HCID 23152337, compound

Product 1

HCID 23152803HCID 23152803, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{1-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-1-methylethyl}-3H-benzimidazole-5-carboxylic acid (0.07 g, 0.12 mmol) in N,N-dimethylformamide (1.0 ml) were successively added 2M dimethylamine-tetrahydrofuran solution (0.30 ml, 0.59 mmol), N-ethyl-N′-3-dimethylaminopropylcarbodiimide hydrochloride (0.03 g, 0.15 mmol) and 1-hydroxybenzotriazole monohydrate (0.02 g, 0.15 mmol) at room temperature, and the mixture was stirred overnight. Saturated aqueous sodium hydrogen carbonate solution, methanol and water were added to the reaction mixture. The precipitate was collected by filtration, washed with water, and dried in vacuo to give N-[1-(6-dimethylcarbamoyl-1H-benzimidazol-2-yl)-1-methylethyl]-12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxamide (0.05 g, yield 63%).

Workup

  1. customat room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f509f4f20ddf462ba90133fae7c8ed4b
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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