HCID 59683498, compound → HCID 59766953, compound

HRID 2389709Notes

Reaction equation

HRID 2389709 reaction equation
[Cl:1][C:2]1[C:3]2[C:48]([F:49])=[CH:47][CH:46]=[C:45]([F:50])[C:4]=2[S:5][C:6]=1[C:7]([N:9]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([C:38](=[O:42])N(C)C)[CH:33]=2)[CH:29]=[CH:28][C:27]=1[O:43][CH3:44])[CH:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1)=[O:8].[CH3:51][Mg]Br>C1COCC1>[C:19]([O:18][C:17](=[O:23])[N:16]([CH:13]1[CH2:12][CH2:11][CH:10]([N:9]([CH2:25][C:26]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([C:38](=[O:42])[CH3:51])[CH:33]=3)[CH:29]=[CH:28][C:27]=2[O:43][CH3:44])[C:7]([C:6]2[S:5][C:4]3[C:45]([F:50])=[CH:46][CH:47]=[C:48]([F:49])[C:3]=3[C:2]=2[Cl:1])=[O:8])[CH2:15][CH2:14]1)[CH3:24])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 59683498HCID 59683498, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59766953HCID 59766953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of dimethyl amide 163 (50 mg, 0.07 mmol) in dry THF (3 ml) at 0° C. was added a 3M solution of methyl magnesium bromide (0.18 ml, 0.55 mmol) in THF. After 1 h, the completed reaction was quenched with 1.2 M HCl, basified and extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, reduced in vacuo and purified by chromatography with 70% EtOAc in heptane to give the title compound.

Workup

  1. customthe completed reaction
  2. customwas quenched with 1.2 M HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. custompurified by chromatography with 70% EtOAc in heptane

Sources & evidence

ORD record
ord-6bb7a34376114782a7442b0f2e44186c
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

Loading…