Acetic Acid → HCID 178489265, compound

HRID 931207Notes

Reaction equation

HRID 931207 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10].C(N(CC)CC)C.C(O)(=O)C.Cl.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1([C:47](=N)OCC)[CH2:46][CH2:45]1>C(O)C>[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1([C:47]2[NH:10][C:9]3=[N:8][C:7]([N:11]4[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]5[CH2:23][CH2:22][CH2:21][CH2:20]5)=[O:18])[CH2:12]4)=[CH:6][CH:5]=[C:4]3[N:3]=2)[CH2:45][CH2:46]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochlorideHCID 89854623Ethyl 1-(2-methoxyphenyl)cyclopropanecarbimidate hydrochloride

Product 1

HCID 178489265HCID 178489265, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (32 mg, 0.088 mmol) in ethanol (0.5 mL) was added triethylamine (50 μL, 1.42 mmol) and acetic acid (82 μL, 1.42 mmol). Then a solution of ethyl 1-(2-methoxyphenyl)cyclopropanecarbimidate hydrochloride (50 mg, 0.09 mmol) in ethanol (0.3 mL) was added and the reaction mixture was heated to 75° C. for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The organic layer was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 446.1; HPLC retention time: 2.299 min (Method A).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via HPLC

Sources & evidence

ORD record
ord-84626f47ca0e4f05820aa09b5cb92670
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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