Sulfur → HCID 178521021, compound

HRID 931323Notes

Reaction equation

HRID 931323 reaction equation
[N:1]1([C:6]2([CH:9]=O)[CH2:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1.[S].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[CH2:21]2)=[N:17][C:18]=1[NH2:19]>C(O)(=O)C>[N:1]1([C:6]2([C:9]3[NH:19][C:18]4=[N:17][C:16]([N:20]5[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([N:28]6[CH2:32][CH2:31][CH2:30][CH2:29]6)=[O:27])[CH2:21]5)=[CH:15][CH:14]=[C:13]4[N:12]=3)[CH2:7][CH2:8]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5362487SulfurHCID 87628351HCID 87628351, compoundHCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 178521021HCID 178521021, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

1-(1H-Imidazol-1-yl)cyclopropanecarbaldehyde (60 mg, 0.44 mmol), sulfur (10 mg), and acetic acid (0.5 mL) were added to the filtrate containing (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone, prepared in the previous step, The reaction mixture was heated at 80° C. for 24 h. The solvent was removed under reduced pressure and the resulting crude material was purified via preparative TLC (10% methanol in dichloromethane) to afford the title compound. MS (ES+APCI) 406.1; LCMS retention time 4.739 min (Method R1).

Workup

  1. customprepared in the previous step
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting crude material was purified via preparative TLC (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f76168ff25aa4f4fa28e077ab00cf766
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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