Triethylamine → HCID 71515673, compound

HRID 2277748Notes

Reaction equation

HRID 2277748 reaction equation
[N:1]([CH3:4])=[C:2]=[O:3].[F:5][C:6]1[C:7]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[O:31][CH3:32])=[N:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][S:20]([CH3:23])(=[NH:22])=[O:21])[CH:14]=2)=[N:10][CH:11]=1.C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+]>[F:5][C:6]1[C:7]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[O:31][CH3:32])=[N:8][C:9]([NH:12][C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:19][S:20]([CH3:23])(=[O:21])=[N:22][C:2]([NH:1][CH3:4])=[O:3])=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 71515605HCID 71515605, compound

Product 1

HCID 71515673HCID 71515673, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

Isocyanatomethane (7.3 μL; 0.12 mmol) was added to a solution of (rac)-5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{3-[(S-methylsulfonimidoyl)methyl]phenyl}pyrimidin-2-amine (50 mg; 0.12 mmol) in DMF (2.0 mL) and triethylamine (17.2 μL; 0.12 mmol) at RT. The batch was stirred for 17 hours at RT. The batch was diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate (2×). The combined organic phases were filtered using a Whatman filter and concentrated. The residue was purified by chromatography (DCM/EtOH 95:5) to give the desired product (24 mg; 0.05 mmol).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. filtrationThe combined organic phases were filtered
  3. filtrationfilter
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (DCM/EtOH 95:5)

Sources & evidence

ORD record
ord-dcd0638842c947da8b3e4b021846497f
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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