Hydrochloric Acid → HCID 178484030, compound

HRID 887831Notes

Reaction equation

HRID 887831 reaction equation
[ClH:1].Cl.N[C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][N:12]2[CH2:16][C@H:15]3[C:17]4[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[CH:21][C:22]=4[O:23][CH2:24][C@@H:14]3[CH2:13]2)[CH2:6][CH2:5]1.[C:27]([BH3-])#[N:28].[Na+].C=O.[C:33](=O)([O-])[O-].[K+].[K+].Cl>CO.O.C(O)C.C(O)(=O)C>[ClH:1].[ClH:1].[CH3:33][N:28]([CH3:27])[C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][N:12]2[CH2:16][C@H:15]3[C:17]4[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[CH:21][C:22]=4[O:23][CH2:24][C@@H:14]3[CH2:13]2)[CH2:6][CH2:5]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 178478680HCID 178478680, compound

Product 1

HCID 178484030HCID 178484030, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.685 g of the compound of Example 1 (1.95 mmol) in 18 ml of methanol there are added, at 0° C., 0.245 g of sodium cyanoborohydride, 0.56 ml of acetic acid and then, dropwise, 0.4 ml of 37% formaldehyde solution in water. After stirring for 4 hours, 2 ml of saturated aqueous potassium carbonate solution are added. After evaporating off the solvents and then diluting with water, the mixture is extracted with ethyl acetate, dried (MgSO4) and evaporated. The residue obtained is purified by chromatography on a silica column using a mixture of dichloromethane/methanol/ammonium hydroxide (80/20/2) as eluant to yield, after converting to a salt in ethanol in the warm state using 1N ethereal HCl, the title product.

Workup

  1. customAfter evaporating off the solvents
  2. additiondiluting with water
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. additiona mixture of dichloromethane/methanol/ammonium hydroxide (80/20/2) as eluant
  9. customto yield

Sources & evidence

ORD record
ord-66715978740f4d8e8334a5d573f87747
Source dataset
uspto-grants-2012_08
Patent number
US08247441B2

Reaction notes

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