Formaldehyde → HCID 68911108, compound

HRID 546504Notes

Reaction equation

HRID 546504 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[NH:21][C:22]([C:24]1[S:32][C:31]3[CH2:30][CH2:29][NH:28][CH2:27][C:26]=3[CH:25]=1)=[O:23])=[O:13])=[CH:6]2.C=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.Cl.O.C(O)(=O)C.C(N(CC)CC)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[NH:21][C:22]([C:24]1[S:32][C:31]3[CH2:30][CH2:29][N:28]([CH3:35])[CH2:27][C:26]=3[CH:25]=1)=[O:23])=[O:13])=[CH:6]2

Participants

10

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 68909347HCID 68909347, compound

Product 1

HCID 68911108HCID 68911108, compoundYield 96.7%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

(±)-cis-N1-[(5-Chloroindol-2-yl)carbonyl]-N2-[(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride (171 mg) was suspended in dichloromethane (10 ml), and triethylamine (0.104 ml) was added to stir the mixture at room temperature for 10 minutes. After acetic acid (0.059 ml) was added to the reaction mixture, a 35% aqueous formaldehyde solution (0.070 ml) and sodium triacetoxyborohydride (118 mg) were added, and the mixture was stirred at room temperature for 30 minutes. After a 1N aqueous solution (3 ml) of sodium hydroxide was added to the reaction mixture, water was added to conduct liquid separation. After the resultant organic layer was dried over anhydrous sodium sulfate, the solvent was then distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane:methanol=50:3) to obtain a colorless foamy substance. This substance was suspended in 1N hydrochloric acid, and the suspension was concentrated under reduced pressure to obtain the title compound (85 mg) as a colorless foamy substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. additionwas added
  3. customliquid separation
  4. dry with materialAfter the resultant organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=50:3)
  7. customto obtain a colorless foamy substance
  8. concentrationthe suspension was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d9057be5bd8453a93caf2f22cffa760
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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