Acetic Acid → HCID 178419830, compound

HRID 2370734Notes

Reaction equation

HRID 2370734 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(N(CC)CC)C.[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.FC(F)(F)C([O-])=O>COC(OC)OC.CN(C=O)C>[CH:26]1([CH2:29][NH:18][C@H:15]2[CH2:14][CH2:13][C@H:12]([O:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[CH:1]=[N:2][CH:3]=[CH:4]4)[CH2:17][CH2:16]2)[CH2:28][CH2:27]1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178511692HCID 178511692, compound

Product 1

HCID 178419830HCID 178419830, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

A suspension of 69.7 mg (0.25 mmol) trans-4-(isoquinolin-6-yloxy)-cyclohexylamine (17), 52.7 μL triethyl amine (1.25 mmol, 5 eq.) and 21 mg cyclopropanecarbaldehyde (0.3 mmol, 1.2 eq.) in 3 mL trimethylorthoformate was stirred at room temperature for 1 h. Then a solution of 321.6 mg sodium triacetoxy borohydride (1.25 mmol, 5 eq) and 72 μL acetic acid (75.1 mg, 1.25 eq) in 2 mL DMF was added. The reduction was complete after 10 min. Then the solvents were removed in vacuo and the product was isolated via preparative HPLC to yield 41 mg of the title compound as trifluoroacetate. Rt=0.89 min (Method #1). Detected mass: 297.3 (M+H+).

Workup

  1. waitThe reduction was complete after 10 min
  2. customThen the solvents were removed in vacuo
  3. customthe product was isolated via preparative HPLC

Sources & evidence

ORD record
ord-5e66a3f834504cf8bb497f6e6a1e8b70
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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