Dimethylformamide → HCID 178513110, compound

HRID 2171720Notes

Reaction equation

HRID 2171720 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][C:13]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)([OH:16])[CH2:12][CH2:11]1.C[N:24](C=O)C.C1N=CN([C:33]([N:35]2[CH:39]=[N:38]C=C2)=[O:34])C=1.C(=O)(O)O.NC(N)=N>O>[C:39]([NH:35][C:33](=[O:34])[O:9][CH2:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N:10]2[CH2:11][CH2:12][C:13]([OH:16])([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)[C:2]=1[F:1])(=[NH:38])[NH2:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 286947Carbonic acid-guanidine (1:1)HCID 68310219HCID 68310219, compound

Product 1

HCID 178513110HCID 178513110, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[2-Fluoro-3-(hydroxymethyl)phenyl]-4-(pyridin-3-yl)piperidin-4-ol (187 mg), DMF (5.5 ml), and CDI (201 mg) were mixed, followed by stirring at room temperature for 2 hours. Guanidine carbonate (279 mg) was added to the reaction mixture, followed by stirring at room temperature overnight. Water was added to the reaction mixture, followed by ice-cooling and stirring for 30 minutes, and the generated solid was collected by filtration, washed with water, and then dried at 50° C. under reduced pressure. The obtained solid was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 2-fluoro-3-[4-hydroxy-4-(pyridin-3-yl)piperidin-1-yl]benzyl carbamimidoylcarbamate (160 mg).

Workup

  1. stirringby stirring at room temperature overnight
  2. temperaturecooling
  3. stirringstirring for 30 minutes
  4. filtrationthe generated solid was collected by filtration
  5. washwashed with water
  6. customdried at 50° C. under reduced pressure
  7. customThe obtained solid was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-d6bc67e9c40d4256b1b64fa8b42b8f06
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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