Isoamylamine → HCID 10018796, compound

HRID 747546Notes

Reaction equation

HRID 747546 reaction equation
[CH:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.[CH3:18][CH:19]([CH3:23])[CH2:20][CH2:21][NH2:22].C([O-])([O-])OC.[BH4-].[Na+]>CO>[CH3:18][CH:19]([CH3:23])[CH2:20][CH2:21][NH:22][CH2:1][C:3]1[S:7][C:6]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 53629101MethylorthoformateHCID 58677395HCID 58677395, compound

Product 1

HCID 10018796HCID 10018796, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(5-formyl-thiophen-2-yloxy)-benzamide (99 mg, 0.40 mmol) from Example 1 part B, method B, with 3-methyl-butylamine (0.056 mL, 0.48 mmol), methyl orthoformate (0.53 mL) and methanol (0.8 mL). Stir the resulting mixture for 3 hours and then add sodium borohydride in portions. Let stir for few hours. Then, concentrate to remove the methanol. Partition the resulting residue between H2O (4 mL) and CH2Cl2 (6 ml). Dry the organic layer over sodium sulfate, filter and concentrate. Purify through flash chromatography [CH2Cl2/Ammonia (2.0 M in methanol) 20/1] to provide the title compound.

Workup

  1. stirringLet stir for few hours
  2. concentrationThen, concentrate
  3. customto remove the methanol
  4. customPartition the resulting residue between H2O (4 mL) and CH2Cl2 (6 ml)
  5. dry with materialDry the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify through flash chromatography [CH2Cl2/Ammonia (2.0 M in methanol) 20/1]

Sources & evidence

ORD record
ord-df3a9c654f164c2bb9d224d8b1f935f4
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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