Ammonium Chloride → HCID 22481693, compound

HRID 2181662Notes

Reaction equation

HRID 2181662 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[CH:9]=[C:10]([C:12](O)=[O:13])[O:11][C:7]=2[CH:6]=1)=[O:4].C[N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN(C=O)C.[Na+].[Cl-]>[NH2:18][C:12]([C:10]1[O:11][C:7]2[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:16]=[CH:15][C:8]=2[CH:9]=1)=[O:13]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69795215HCID 69795215, compound

Product 1

HCID 22481693HCID 22481693, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

6-(Methoxycarbonyl)-1-benzofuran-2-carboxylic acid (220 mg, 1.0 mmol) is combined with HATU (570 mg, 1.5 mmol) in DMF (4 mL). The mixture is treated portionwise with DIEA (350 μL, 2.0 mmol) and NH4Cl (183 mg, 3.4 mmol) and stirred for 3 h. The mixture is diluted with saturated NaCl (50 mL) and extracted with EtOAc (3×20 mL). The combined organics are washed with 2N HCl (2×10 mL), followed by water (2×10 mL), saturated NaHCO3 (2×10 mL) and additional H2O (2×10 mL) then dried (Na2SO4) and concentrated to afford 177 mg (81%) of methyl 2-(aminocarbonyl)-1-benzofuran-6-carboxylate as an orange-brown solid. HRMS (FAB) calcd for C11H9NO4+H: 220.0610, found 220.0603 M+H)+.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organics are washed with 2N HCl (2×10 mL)
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b097c372d45a4c8eb26f40417e0db713
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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