Ammonia → HCID 86624364, compound

HRID 341409Notes

Reaction equation

HRID 341409 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=NO)=[C:24]([Cl:29])[N:23]=[C:22]3[O:30][CH2:31][CH3:32])=[C:16]([F:33])[CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH3-]C#N.[Na+].C([O-])(=[O:40])C.[NH4+].N>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=[O:40])=[C:24]([Cl:29])[N:23]=[C:22]3[O:30][CH2:31][CH3:32])=[C:16]([F:33])[CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86626266HCID 86626266, compound

Product 1

HCID 86624364HCID 86624364, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent2×

Procedure

Titanium(III) chloride (448 mg, 2.90 mmol) was added to a solution of intermediate (27b) (459.0 mg, 1.0 mmol), NaBH3CN (274 mg, 4.4 mmol) and ammonium acetate (164 mg, 2.1 mmol) in MeOH (8 mL) at 0° C. The mixture was stirred at room temperature for 3 hours. The mixture was added to a solution of sat. aq. ammonia (15 mL) and MeOH (15 mL). The solution was filtered, and concentrated in vacuo. The concentrate was extracted with DCM (2×80 mL) and sat. aq. NaHCO3 (50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography [DCM:MeOH (5% triethylamine)] afforded the title compound (85 mg).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. extractionThe concentrate was extracted with DCM (2×80 mL) and sat. aq. NaHCO3 (50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81e4c62fa17341298ad21bcedc3cd01c
Source dataset
uspto-grants-2014_11
Patent number
US08895755B2

Reaction notes

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