Acetic Acid → HCID 178481924, compound

HRID 931331Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:10]2)=[N:6][C:7]=1[NH2:8].[CH3:22][N:23]1[C:27]([C:28]2([C:31](=N)OCC)[CH2:30][CH2:29]2)=[N:26][CH:25]=[N:24]1.[S].C(O)(=O)C>C(O)C>[CH3:22][N:23]1[C:27]([C:28]2([C:31]3[NH:8][C:7]4=[N:6][C:5]([N:9]5[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]6[CH2:21][CH2:20][CH2:19][CH2:18]6)=[O:16])[CH2:10]5)=[CH:4][CH:3]=[C:2]4[N:1]=3)[CH2:30][CH2:29]2)=[N:26][CH:25]=[N:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone, prepared during the previous step, was added to a suspension of ethyl 1-(1-methyl-1H-1,2,4-triazol-5-yl)cyclopropanecarbimidate (0.39 g, 2.0 mmol), sulfur (20 mg, 0.31 mmol) and acetic acid (0.96 mL, 15.5 mmol) in ethanol (10 mL) at room temperature. The reaction mixture was heated to 80° C. for 16 h. The mixture was concentrated under reduced pressure and the resulting crude was dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude was purified via preparative TLC to afford the title compound (120 mg, 18%). MS (ES+APCI) (M+H) 421.2; LCMS retention time: 3.311 min (Method Y1).

Workup

concentrationThe mixture was concentrated under reduced pressure
dissolutionthe resulting crude was dissolved in ethyl acetate
washwashed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting crude was purified via preparative TLC

Sources & evidence

ORD record: ord-4d9bcec14d124f7b9bf20d25a9fe2615
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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