Potassium Carbonate → HCID 178452760, compound

HRID 1363208Notes

Reaction equation

HRID 1363208 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:10]([NH:22][C:23]2[N:28]=[C:27](SC#N)[C:26]([N+:32]([O-:34])=[O:33])=[CH:25][N:24]=2)[CH:9]=1.[OH:35][C@H:36]1[CH2:41][CH2:40][C@H:39]([NH2:42])[CH2:38][CH2:37]1>C(#N)C.C(Cl)Cl>[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[C:10]([NH:22][C:23]2[N:28]=[C:27]([NH:42][C@H:39]3[CH2:40][CH2:41][C@H:36]([OH:35])[CH2:37][CH2:38]3)[C:26]([N+:32]([O-:34])=[O:33])=[CH:25][N:24]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59704889tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamateHCID 178511715HCID 178511715, compound

Product 1

HCID 178452760HCID 178452760, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium carbonate (105 mg) was added to a stirred mixture of tert-butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenyl-carbamate (101 mg) in acetonitrile (5 ml) followed by the addition of trans-4-hydroxycyclohexylamine (44 mg). The reaction mixture was stirred for 16 hours, then diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to provide 110 mg of the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e90d4bdfe3e454eba2c3b1a2a1c29ae
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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