Sodium Bicarbonate → HCID 68640530, compound

HRID 1809457Notes

Reaction equation

HRID 1809457 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17](OC)=[O:18])[N:12]3[C:21]=2[CH:22]=O)=[CH:5][CH:4]=1)#[N:2].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:27]=1[CH2:28][NH2:29].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CO.C(Cl)Cl>[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:27]=1[CH2:28][N:29]1[C:17](=[O:18])[C:13]2[N:12]3[C:21](=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=2)[CH2:22]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 5003444Sodium cyanoborohydrideHCID 86651539HCID 86651539, compound

Product 1

HCID 68640530HCID 68640530, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (B1) in MeOH (0.2 M), 2,4-dimethoxybenzylamine (1.2 eq.) and Ti(iPrO)4 (2.0 eq.) were added and the reaction mixture was stirred at RT for 2 h. Then, NaBH3CN (1.5 eq.) was added and stirring was continued for 24 h. The solvent was reduced in vacuo and the residue pardoned between sat. aq. NaHCO3 and DCM. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by flash column on silica using a gradient of EtOAc/Petroleum ether from 50:50 to 70:30 to yield (55%) the title compound as a yellow powder. 1H NMR (600 MHz, DMSO-d6, 330K) δ 7.94 (2H, d, J=8.6 Hz), 7.90 (2H, d, J=8.6 Hz), 7.72 (1H, d, J=9.0 Hz), 7.47 (1H, d, J=7.0 Hz), 7.35 (1H, dd, J=8.4, 7.0 Hz), 7.23 (1H, d, J=8.3 Hz), 6.61 (1H, d, J=2.0 Hz), 6.48 (1H, dd, J=8.3, 2.0 Hz), 5.38 (2H, s), 4.72 (2H, s), 3.86 (3H, s), 3.74 (3H, s). MS (ES+) C25H20N4O3 requires: 424, found: 425 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 24 h
  3. customThe aqueous phase was separated
  4. extractionextracted several times with DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave a residue which
  9. customwas purified by flash column on silica using a gradient of EtOAc/Petroleum ether from 50:50 to 70:30

Sources & evidence

ORD record
ord-ca3d16e9fd134b35985a640bdc580894
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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