Trifluoroacetic acid → N-(4-(7-((1-(3-methoxypropanoyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

HRID 1188266Notes

Reaction equation

HRID 1188266 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]#[C:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:28])[C:12]([C:17]4[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=4)=[CH:13][O:14]3)=[CH:9][CH:8]=2)[CH2:2]1.FC(F)(F)C(O)=O.[CH3:36][O:37][CH2:38][CH2:39][C:40](O)=[O:41].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.O.C(#N)C>[CH3:36][O:37][CH2:38][CH2:39][C:40]([N:1]1[CH2:4][CH:3]([C:5]#[C:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:28])[C:12]([C:17]4[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=4)=[CH:13][O:14]3)=[CH:9][CH:8]=2)[CH2:2]1)=[O:41]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1344423-Methoxypropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71506445N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Product 1

HCID 71506635N-(4-(7-((1-(3-methoxypropanoyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide.trifluoroacetic acid salt (80 mgs, 0.16 mmol), 3-methoxypropanoic acid (0.03 mL, 0.24 mmol), HATU (91 mgs, 0.24 mmol), in N,N-dimethylformamide (1 mL) was added diisopropylethylamine (0.1 mL, 0.41 mmol) and the mixture stirred at room temperature for 16 hours. The reaction mixture was diluted with water and acetonitrile, and the resulting solid was filtered and washed with acetonitrile and ether and dried to give N-(4-(7-((1-(3-methoxypropanoyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide:

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with acetonitrile and ether
  3. customdried

Sources & evidence

ORD record
ord-07d2caec63244dd19f17617e2155e0f3
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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