Ammonium Chloride → HCID 44187340, compound

HRID 1802818Notes

Reaction equation

HRID 1802818 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[NH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[Cl:19][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([NH:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[CH:14]=1)[NH:11][C:10]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1)=[CH:18]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 44187341HCID 44187341, compound

Product 1

HCID 44187340HCID 44187340, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound obtained in Example 64 (760 mg, 2.06 mmol) was dissolved in 30 ml of tetrahydrofuran and 2M-lithiumborohydride solution in tetrahydrofuran (2.06 ml, 4.12 mmol) was added. The mixture was at 80° C. for 3 hours. Saturated ammoniumchloride solution was added and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to obtain the title compound 60 mg (Yield 9%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationThe filtrate was distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-750c13a0df7d4295a66693bac95c1f7f
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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