Acetic Acid → HCID 69227246, compound

HRID 916323Notes

Reaction equation

HRID 916323 reaction equation
[ClH:1].[C@H:2]12[CH2:8][C@H:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=1.C=O.[C:23](O)(=O)C.C([BH3-])#N.[Na+]>CO.[OH-].[Na+].O>[ClH:1].[CH3:23][N:6]1[CH2:7][C@@H:2]2[CH2:8][C@H:5]1[CH2:4][N:3]2[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11637791HCID 11637791, compound

Product 1

HCID 69227246HCID 69227246, compound

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

165RL09 (26.4 mg, 0.106 mmol) was dissolved in methanol (5 mL) and formaldehyde (37% in water, 16 μL, 0.21 mmol) was added. The mixture was acidified by adding acetic acid (10 μL). After 5 min of shaking, sodium cyanoborohydride (46.6 mg, 0.741 mmol) was added and the mixture was allowed to react for 2 hours. The mixture was hydrolyzed by adding 5 drops of sodium hydroxide (2M) followed by water (10 mL) and the mixture extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to dryness. The product (23 mg, 83%) needed no further purification and was converted to the corresponding hydrochloride salt as described above.

Workup

  1. customto react for 2 hours
  2. extractionthe mixture extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customno further purification

Sources & evidence

ORD record
ord-d0caef9a9b8c482f9540249ccf232505
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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