Benzofuran-2-carboxylic acid → HCID 178456941, compound

HRID 1620715Notes

Reaction equation

HRID 1620715 reaction equation
Cl.Cl.[CH2:3]([NH:6][C:7]1=[N:8][C:9](=[O:19])[S:10]/[C:11]/1=[CH:12]\[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:4]#[CH:5].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:53]1[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[CH:55]=[C:54]1[C:62](O)=[O:63]>CN(C=O)C.O>[O:53]1[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[CH:55]=[C:54]1[C:62]([N:16]1[CH2:17][CH2:18][CH:13](/[CH:12]=[C:11]2/[C:7]([NH:6][CH2:3][C:4]#[CH:5])=[N:8][C:9](=[O:19])[S:10]/2)[CH2:14][CH2:15]1)=[O:63]

Participants

7

Reactant 4

HCID 10331Benzofuran-2-carboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178456897HCID 178456897, compound

Product 1

HCID 178456941HCID 178456941, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (5Z)-4-(prop-2-yn-1-ylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) in DMF (3 mL) were added N-ethyl-N-(1-methylethyl)propan-2-amine (0.56 mL), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (283 mg), and benzofuran-2-carboxylic acid (124 mg). The reaction mixture was stirred at room temperature overnight, water was added, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/heptane to give the title compound (167 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-54aa4def5100442ab946803e8b3256c1
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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