Acetic Acid → HCID 178419984, compound

HRID 931228Notes

Reaction equation

HRID 931228 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=O)[CH2:12]2)=[N:8][C:9]=1[NH2:10].C(O)(=O)C.[CH2:28]([N:30](CC)CC)C.[CH:35]1([C:38]2[N:43]=[C:42]([C:44](=N)OCC)[CH:41]=[CH:40][N:39]=2)[CH2:37][CH2:36]1>C(O)C>[CH:35]1([C:38]2[N:43]=[C:42]([C:44]3[NH:10][C:9]4=[N:8][C:7]([N:11]5[CH2:16][CH2:15][CH2:14][CH:13]([C:17]6[N:19]7[CH2:23][CH2:22][CH2:21][C:20]7=[CH:28][N:30]=6)[CH2:12]5)=[CH:6][CH:5]=[C:4]4[N:3]=3)[CH:41]=[CH:40][N:39]=2)[CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89853790(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochlorideHCID 89854162Ethyl 2-cyclopropylpyrimidine-4-carbimidate

Product 1

HCID 178419984HCID 178419984, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of (1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (18 mg, 0.06 mmol) and acetic acid (55 μL, 0.96 mmol) in ethanol (0.5 mL) was added triethylamine (17 μL, 0.12 mmol) followed by ethyl 2-cyclopropylpyrimidine-4-carbimidate (11.5 mg, 0.06 mmol) dissolved in ethanol (0.5 mL). The reaction mixture was heated to 70° C. for 1.25 h. The solvent was removed under reduced pressure. The residue was suspended in ethyl acetate and the undissolved solids were filtered off. The filtrate was washed with a saturated aqueous solution of ammonium chloride, washed with a saturated aqueous solution of sodium bicarbonate, and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 427.1; HPLC retention time 2.0183 (Method A).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe undissolved solids were filtered off
  3. washThe filtrate was washed with a saturated aqueous solution of ammonium chloride
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. washwashed with brine
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified via HPLC

Sources & evidence

ORD record
ord-a22db86a9f0c41c993bf0a509ed7154a
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…