Acetic Acid → HCID 178489647, compound

HRID 931209Notes

Reaction equation

HRID 931209 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(O)(=O)C.C(N(CC)CC)C.Cl.[CH3:36][O:37][C:38]1[CH:39]=[C:40]([C:44]2([C:47](=N)OCC)[CH2:46][CH2:45]2)[CH:41]=[CH:42][CH:43]=1>CO>[CH3:36][O:37][C:38]1[CH:39]=[C:40]([C:44]2([C:47]3[NH:10][C:9]4=[N:8][C:7]([N:11]5[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]6[CH2:23][CH2:22][CH2:21][CH2:20]6)=[O:18])[CH2:12]5)=[CH:6][CH:5]=[C:4]4[N:3]=3)[CH2:45][CH2:46]2)[CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89853434HCID 89853434, compoundHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Product 1

HCID 178489647HCID 178489647, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
130 °C

Procedure

To a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (60 mg, 0.17 mmol) in methanol (0.5 mL) and acetic acid (150 μL, 2.7 mmol) was added triethylamine (94 μL, 0.67 mmol) and a solution of ethyl 1-(3-methoxyphenyl)cyclopropanecarbimidate hydrochloride (40 mg, 0.16 mmol) in methanol (0.3 mL). The reaction mixture was heated in a microwave for 45 min at 130° C. 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) 446.3; HPLC retention time 2.3 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-42e1180b9179457fb1a6672c87f19d9b
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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