Phenyl chloroformate → HCID 89717155, compound

HRID 1771537Notes

Reaction equation

HRID 1771537 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=1)[CH2:2]2.C(=O)([O-])O.[Na+].Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>C(Cl)Cl.CCOC(C)=O>[C:31]1([O:30][C:28](=[O:29])[NH:19][C:18]2[CH:20]=[CH:21][C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([N:3]4[CH2:4][CH:5]5[O:8][CH:1]([CH2:7][CH2:6]5)[CH2:2]4)[N:14]=3)=[CH:16][CH:17]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 67382726HCID 67382726, compound2×

Product 1

HCID 89717155HCID 89717155, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-4-yl)aniline (intermediate 26) (471 mg, 1.51 mmol) was stirred with sodium hydrogen carbonate (190 mg, 2.26 mmol) and phenyl chloroformate (285 μl, 2.26 mmol) in DCM (5 ml) at room temperature overnight. The reaction mixture was diluted with EtOAc, washed with brine and the organics were concentrated in vacuo. The resulting yellow solid was purified by flash chromatography (0-100% EtOAc:Petroleum Ether 40-60) to afford the title compound. (60 mg, 10%)

Workup

  1. washwashed with brine
  2. concentrationthe organics were concentrated in vacuo
  3. customThe resulting yellow solid was purified by flash chromatography (0-100% EtOAc:Petroleum Ether 40-60)

Sources & evidence

ORD record
ord-c31cada7436a4072931a698cf7981d02
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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