Cesium carbonate → HCID 70978060, compound

HRID 2281047Notes

Reaction equation

HRID 2281047 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:25]=[CH:24][C:16]3[N:17]([CH2:20][CH:21]4[CH2:23][CH2:22]4)[N:18]=[N:19][C:15]=3[C:14]=2[C:26]([F:29])([F:28])[F:27])=[CH:9][CH:8]=1)(=O)=O.Cl.[NH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH:21]1([CH2:20][N:17]2[C:16]3[CH:24]=[CH:25][C:13]([C:10]4[CH:11]=[CH:12][C:7]([CH2:6][NH:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:8][CH:9]=4)=[C:14]([C:26]([F:29])([F:27])[F:28])[C:15]=3[N:19]=[N:18]2)[CH2:23][CH2:22]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 86711981HCID 86711981, compound

Product 1

HCID 70978060HCID 70978060, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]benzyl methanesulfonate (0.12 mg, 0.28 mmol) was dissolved in acetonitrile (2.8 mL) and treated the mixture with ethyl aminoacetate hydrochloride (150 mg, 1.1 mmol), cesium carbonate (270 mg, 0.824 mmol) and tetra-n-butylammonium iodide (51 mg, 0.14 mmol). The mixture was placed into an oil bath preheated to 85° C. and stirred for 2 h, at which time the mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with sodium bicarbonate (2×30 mL, aqueous saturated). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC (85:15 to 42:58; water with 0.05% trifluoroacetic acid:acetonitrile with 0.05% trifluoroacetic acid) to afford the titled compound.

Workup

  1. customThe mixture was placed into an oil bath
  2. custompreheated to 85° C.
  3. washwashed with sodium bicarbonate (2×30 mL, aqueous saturated)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase preparative HPLC (85:15 to 42:58; water with 0.05% trifluoroacetic acid:acetonitrile with 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-f28519f9d93b48e68947e8f23340c8a6
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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