Hydrochloric Acid → HCID 69428691, compound

HRID 1270001Notes

Reaction equation

HRID 1270001 reaction equation
[C:1](O)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.[CH3:37][C:38]1[C:46]([O:47][C@@H:48]2[CH2:53][CH2:52][CH2:51][C@H:50]([NH2:54])[CH2:49]2)=[CH:45][CH:44]=[C:43]2[C:39]=1[CH:40]=[N:41][NH:42]2>CN(C)C=O>[CH3:3][CH:2]([CH3:4])[C:1]([NH:54][C@H:50]1[CH2:51][CH2:52][CH2:53][C@@H:48]([O:47][C:46]2[C:38]([CH3:37])=[C:39]3[C:43](=[CH:44][CH:45]=2)[NH:42][N:41]=[CH:40]3)[CH2:49]1)=[O:5]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6590Isobutyric AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69431191HCID 69431191, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 69428691HCID 69428691, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isobutyric acid (36.2 μL, 0.39 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (74.8 mg, 0.39 mmol), hydroxybenzotriazole (52.8 mg, 0.39 mmol) and triethylamine (0.18 ml, 1.28 mmol) were added to a solution of monohydrochloride (100 mg, 0.35 mmol) of the cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine obtained in Example 411 in N,N-dimethylformamide (5 ml), and the resulting mixture was stirred overnight at room temperature. The reaction solution was partitioned by the addition of ethyl acetate, toluene and water, and then extracted twice with ethyl acetate-toluene (1/1). The extract solution was washed with a saturated aqueous sodium hydrogencarbonate solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=1/1 to 0/1) to obtain 2-methyl-N-{cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}propanamide (86.3 mg, 77%).

Workup

  1. customThe reaction solution was partitioned by the addition of ethyl acetate, toluene and water
  2. extractionextracted twice with ethyl acetate-toluene (1/1)
  3. washThe extract solution was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=1/1 to 0/1)

Sources & evidence

ORD record
ord-f766769cee2a4f82bccaa1e701a8a35d
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…