HCID 178418443, compound → HCID 178461554, compound

HRID 1777738Notes

Reaction equation

HRID 1777738 reaction equation
C[O:2][C:3]([C:5]1[CH:41]=[CH:40][C:8]2[NH:9][C:10]([C:12]3[N:13]=[C:14]([C:36]([F:39])([F:38])[F:37])[S:15][C:16]=3[N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:34])[CH2:24][N:25]4[C:29]5=[N:30][CH:31]=[CH:32][CH:33]=[C:28]5[N:27]=[CH:26]4)[C@H:19]([CH3:35])[CH2:18]3)=[N:11][C:7]=2[CH:6]=1)=O.[CH2:42]([Mg]Br)[CH3:43]>C1COCC1.C(Cl)Cl.C([O-])(O)=O.[Na+].CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[OH:2][C:3]1([C:5]2[CH:41]=[CH:40][C:8]3[NH:9][C:10]([C:12]4[N:13]=[C:14]([C:36]([F:37])([F:38])[F:39])[S:15][C:16]=4[N:17]4[CH2:22][CH2:21][N:20]([C:23](=[O:34])[CH2:24][N:25]5[C:29]6=[N:30][CH:31]=[CH:32][CH:33]=[C:28]6[N:27]=[CH:26]5)[C@H:19]([CH3:35])[CH2:18]4)=[N:11][C:7]=3[CH:6]=2)[CH2:43][CH2:42]1

Participants

7

Reactant 2

HCID 178418443HCID 178418443, compoundHCID 178497348HCID 178497348, compound

Product 1

HCID 178461554HCID 178461554, compound

Reagents, catalysts & solvents 4

HCID 178460666HCID 178460666, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of Example 167 (25 mg) in THF (1.15 mL) was added Ti(OiPr)4 (0.0126 mL). Ethylmagnesium bromide (1M in THF, 0.513 mL) was added dropwise over 30 min at RT. The reaction mixture was stirred at RT for 20 h and diluted with DCM and 1M NaHCO3. The phases were separated. The org. phase was washed with water, dried (Na2SO4), filtered off and evaporated in vacuo. The residue was purified by preparative LC-MS (III) to afford 1 mg of pale yellow solid. LC-MS (B): tR=0.65 min; [M+H]+: 583.18.

Workup

  1. customThe phases were separated
  2. washphase was washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered off
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative LC-MS (III)

Sources & evidence

ORD record
ord-d03d039eecf444798a5a7395bca7b590
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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