Triethylamine → HCID 59380058, compound

HRID 2353726Notes

Reaction equation

HRID 2353726 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[N:14]=[C:13](Cl)[CH:12]=[C:11]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[N:10]=1.[CH3:27][C@H:28]1[CH2:33][O:32][CH2:31][CH2:30][NH:29]1>C(Cl)Cl>[Cl:8][C:9]1[N:10]=[C:11]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:12]=[C:13]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][C@@H:28]2[CH3:27])[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12012220(3S)-3-methylmorpholineHCID 57427821HCID 57427821, compound

Product 1

HCID 59380058HCID 59380058, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (1.117 ml, 8.01 mmol) was added to 2,4-dichloro-6-[(4-fluorophenyl)sulfonylmethyl]pyrimidine (2.34 g, 7.29 mmol) in DCM (36.4 mL) at 0° C. followed by (3S)-3-methylmorpholine (0.737 g, 7.29 mmol) in DCM (20 mL) over 15 minutes. The reaction was then stirred at RT for 16 hours. The reaction mixture was washed with water (50 mL), the organic layer dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% ethyl acetate in DCM, to give the desired material as a beige solid (1.530 g).

Workup

  1. washThe reaction mixture was washed with water (50 mL)
  2. dry with materialthe organic layer dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-f4fc8c997aa6402dbcfa775c192a9e8f
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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