Methyl iodide → HCID 89861084, compound

HRID 879513Notes

Reaction equation

HRID 879513 reaction equation
[C:1](O)(C(F)(F)F)=O.[C:8]([O:12][C@@H:13]([C:17]1[C:38]([CH3:39])=[CH:37][C:20]2[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4C=NC(=O)[NH:34][CH:35]=4)[CH:25]=3)[S:23][C:19]=2[C:18]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:14]([OH:16])=[O:15])([CH3:11])([CH3:10])[CH3:9].C([O-])([O-])=O.[K+].[K+].CI.C[C:56]([N:58]([CH3:60])[CH3:59])=[O:57]>>[C:8]([O:12][C@@H:13]([C:17]1[C:38]([CH3:39])=[CH:37][C:20]2[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[CH:35]=[N:34][C:56](=[O:57])[N:58]([CH3:60])[CH:59]=4)[CH:25]=3)[S:23][C:19]=2[C:18]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:14]([O:16][CH3:1])=[O:15])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 89860453HCID 89860453, compound

Product 1

HCID 89861084HCID 89861084, compound

Procedure

To the TFA salt of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(2-oxo-1,2-dihydropyrimidin-5-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid (94.8 mg, 0.141 mmol) in DMA (3.0 mL) was added K2CO3 (194.4 mg, 1.406 mmol) and methyl iodide (199.6 mg, 0.088 mL, 1.406 mmol). The reaction was stirred at room temperature for 45 minutes, filtered through Celite (ethyl acetate eluent), concentrated, and used without further purification. LCMS-ESI+: calc'd for C32H31ClN3O4S (M+H1): 588.2; Found: 588.2 (M+H+).

Workup

  1. filtrationfiltered through Celite (ethyl acetate eluent)
  2. concentrationconcentrated
  3. customused without further purification

Sources & evidence

ORD record
ord-c5c262addd2b4e24bb55821f8efb987b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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