Acetic Acid → HCID 11260730, compound

HRID 1243778Notes

Reaction equation

HRID 1243778 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)[OH:4].[NH2:14][C:15]1[C:23]2[C:18](=[N:19][C:20]([N:27]3[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]3)=[CH:21][C:22]=2[CH2:24][CH2:25][CH3:26])[S:17][C:16]=1[C:34]([NH2:36])=[O:35].[BH4-].C(O)(=O)C>C1COCC1.CO>[NH2:14][C:15]1[C:23]2[C:18](=[N:19][C:20]([N:27]3[CH2:28][CH2:29][CH:30]([NH:1][CH2:2][CH:3]([C:5]4[S:9][C:8]5[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=5[CH:6]=4)[OH:4])[CH2:31][CH2:32]3)=[CH:21][C:22]=2[CH2:24][CH2:25][CH3:26])[S:17][C:16]=1[C:34]([NH2:36])=[O:35]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 28123BorohydrideHCID 2756344HCID 2756344, compoundHCID 9840574HCID 9840574, compound

Product 1

HCID 11260730HCID 11260730, compoundYield 27.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above 2-amino-1-benzo[b]thiophen-2-yl-ethanol (57.9 mg, 0.300 mmol), 3-amino-6-(4-oxo-piperidin-1-yl)-4-propyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (50.0 mg, 0.15 mmol), MP-borohydride (100 mg) and acetic acid (0.075 mL, 1.31 mmol) were mixed in a 2-dram vial in THF (4 mL) and shaken at room temperature for 21 h overnight. The reaction was filtered, and the borohydride resin was rinsed with MeOH, and then filtered again. The combined filtrates were concentrated in on a rotary evaporator to afford crude product. The residue was dissolved into a minimal amount of MeOH, applied to a 1 mm prep plate (Merck) and eluted with 5% MeOH/CH2Cl2, 1% NH3 to give 21.3 mg, 27.9% of the title compound. ES+ 510.1 m/z (MH+).

Workup

  1. filtrationThe reaction was filtered
  2. washthe borohydride resin was rinsed with MeOH
  3. filtrationfiltered again
  4. concentrationThe combined filtrates were concentrated in on a rotary evaporator
  5. customto afford crude product
  6. washeluted with 5% MeOH/CH2Cl2, 1% NH3

Sources & evidence

ORD record
ord-99f901bd81974d53a38ca6aaa158071d
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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