Carbon Dioxide → HCID 67148661, compound

HRID 2234102Notes

Reaction equation

HRID 2234102 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH:18]=O)[CH:15]=2)[CH:10]=[C:9]1[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=[N:22][C:21]=1[O:32]C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1C2C(=CC=C(CC=O)C=2)C=C1C1C(=O)NN=C([C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)C=1)=O)(C)(C)C.N1CCOCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].C(=O)=O>ClC(Cl)C.ClCCl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][CH:61]3[CH2:60][CH2:59][CH2:64][CH2:63][NH:62]3)[CH:15]=2)[CH:10]=[C:9]1[C:20]1[C:21](=[O:32])[NH:22][N:23]=[C:24]([C:26]2[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=2)[CH:25]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

10

Reactant 6

HCID 280Carbon DioxideHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86612053HCID 86612053, compoundHCID 86612054HCID 86612054, compound

Product 1

HCID 67148661HCID 67148661, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

54 mg of a mixture of 6-(2-oxoethyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester and 6-(2-oxoethyl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)indole-1-carboxylic acid tert-butyl ester are dissolved in 9 mL dichloroethane. 160 □L morpholine and then 0.46 mL acetic acid are added. 129 mg sodium triacetoxyborohydride are added in several portions over 4 hours. Sat. aq. NaHCO3-solution is added and the reaction mixture is stirred until the CO2-evolution stopped. The reaction mixture is diluted with dichloromethane, the aq. phase washed with dichloromethane, the combined org. phases dried (MgSO4) and concentrated in vacuo. 8 mg (13%) crude product (mixture of 6-(2-piperidylethyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester and 2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-6-(2-piperidyl-ethyl)-indole-1-carboxylic acid tert-butyl ester is obtained, which is directly used in the next step.

Workup

  1. washthe aq. phase washed with dichloromethane
  2. dry with materialphases dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. addition8 mg (13%) crude product (mixture of 6-(2-piperidylethyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

Sources & evidence

ORD record
ord-ed14c226dd3247c8982e3349cab4bd08
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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