Triethylamine → HCID 59856644, compound

HRID 1174774Notes

Reaction equation

HRID 1174774 reaction equation
Cl.[F:2][C:3]1[CH:23]=[C:22]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[CH:20][C:4]=1[O:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:9]=[CH:8][N:7]=1.Br[CH2:29][C:30](=[O:33])[CH2:31][CH3:32].C(N(CC)CC)C>CN(C=O)C>[F:2][C:3]1[CH:23]=[C:22]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=[CH:20][C:4]=1[O:5][C:6]1[N:7]=[CH:8][N:9]=[C:10]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:29][C:30](=[O:33])[CH2:31][CH3:32])[CH2:16][CH2:15]2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131561-Bromo-2-butanoneHCID 67203341HCID 67203341, compound

Product 1

HCID 59856644HCID 59856644, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Fluoro-4-methanesulfonyl-phenoxy)-5-methyl-6-(piperidin-4-yloxy)-pyrimidine hydrochloride salt (42 mg, 0.1 mmol), 1-bromo-butan-2-one (0.1 mmol, 1 eq), and triethylamine (0.2 mmol, 2 eq) were dissolved in DMF (1 mL) and then stirred at room temperature overnight. The crude was filtered and then purified via prep-LCMS 5-95% to provide Compound C93 as an oil (39.6 mg, 88%). Exact mass calculated for C21H26FN3O5S 451.2, found 452.3 (MH+).

Workup

  1. filtrationThe crude was filtered
  2. custompurified via prep-LCMS 5-95%

Sources & evidence

ORD record
ord-1146bd00a79245b0b1a495d3fecbd9f6
Source dataset
uspto-grants-2010_11
Patent number
US07838525B2

Reaction notes

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