Hydrochloric Acid → HCID 89657342, compound

HRID 1775211Notes

Reaction equation

HRID 1775211 reaction equation
[O:1]=[C:2]1[C:14]2[C:13]3[C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][NH:4][CH2:3]1.[BH3-][C:20]#N.[Na+].C=O.Cl>CO.O>[CH3:20][N:4]1[CH2:3][C:2](=[O:1])[C:14]2[C:13]3[C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 89657350HCID 89657350, compound

Product 1

HCID 89657342HCID 89657342, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-oxo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-5-carboxylate (0.04 g, 0.016 mmol) and NaCNBH3 (2.4 mg, 0.04 mmol) were added to a round bottomed flask, which were then dissolved in MeOH (2 mL), and treated with 0.5 mL of a 27% solution of formaldehyde in water. This mixture was stirred for 2 h, after which, 2N HCl (2 mL) was added, followed by stirring for 15 min. The mixture was taken to pH=11 by addition of concentrated, aqueous NaOH and extracted with methylene chloride (3×10 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The crude product was used in the next step without further purification.

Workup

  1. stirringby stirring for 15 min
  2. additionThe mixture was taken to pH=11 by addition
  3. concentrationof concentrated
  4. extractionaqueous NaOH and extracted with methylene chloride (3×10 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-4755ef8352174d1b9247d4efd7912432
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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