Triethylamine → HCID 59598327, compound

HRID 2265952Notes

Reaction equation

HRID 2265952 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:5]([C:15]#[CH:16])[CH:4]=1.C(N(CC)CC)C.[Cl:24][C:25]1[N:30]=[CH:29][C:28]([O:31][CH2:32][C:33](O)=[O:34])=[CH:27][CH:26]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C1COCC1.CCOC(C)=O>[Cl:24][C:25]1[N:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([NH:1][CH2:2][C:3]2[CH:8]=[C:7]([F:9])[C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:5]([C:15]#[CH:16])[CH:4]=2)=[O:34])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 54289059HCID 54289059, compoundHCID 59389713N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide

Product 1

HCID 59598327HCID 59598327, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide (74.3 mg, 0.266 mmol) was suspended in THF and treated with triethylamine (27 mg, 0.266 mmol) and then the resulting mixture was stirred for 10 mins. (6-chloro-pyridin-3-yloxy)-acetic acid (50 mg, 0.266 mmol) was added to the reaction mixture followed by DMTMM (62.5 mg, 0.266 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat'd NaHCO3 (×3), and brine, and then dried over anh. MgSO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized (CH2Cl2) to yield the title compound (25 mg, 25%).

Workup

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. washThe resulting solution was washed successively with water, sat'd NaHCO3 (×3), and brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was recrystallized (CH2Cl2)

Sources & evidence

ORD record
ord-b1e61635de1f4b1fa3b0b49849d94998
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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