Triethylamine → HCID 68769927, compound

HRID 1947545Notes

Reaction equation

HRID 1947545 reaction equation
Cl.[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[O:11][C:12]1[CH:23]=[CH:22][C:15]2[C:16]([C:19](Cl)=[O:20])=[CH:17][O:18][C:14]=2[CH:13]=1.C[CH2:25][N:26](CC)CC.Cl.Cl.CN.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:25][NH:26][C:19]([C:16]1[C:15]2[CH:22]=[CH:23][C:12]([O:11][C:3]3[S:2][C:10]4[C:5]([N:4]=3)=[N:6][CH:7]=[CH:8][CH:9]=4)=[CH:13][C:14]=2[O:18][CH:17]=1)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 13000547HCID 13000547, compoundHCID 86647610HCID 86647610, compound

Product 1

HCID 68769927HCID 68769927, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-carbonyl chloride hydrochloride (256 mg, 0.77 mmol) in CH2Cl2 (7.7 mL) was added Et3N (0.32 mL, 2.32 mmol) and methylamine dihydrochloride (81 mg, 0.77 mmol). The reaction mixture was stirred (rt, 1 h). Water followed by sat'd. aq. NaHCO3 was added to the mixture. The resultant precipitate was filtered and concentrated to provide the title compound (115 mg, 45%). MS (ESI): mass calcd. for C16H11N3O3S, 325.05; m/z found, 326.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.23 (s, 1H), 8.17-8.01 (m, 2H), 7.37 (dd, J=8.6, 2.2, 1H), 7.24 (dd, J=7.9, 4.8, 1H), 7.01 (d, J=26.5, 1H), 3.00 (d, J=4.8, 3H).

Workup

  1. filtrationThe resultant precipitate was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9368f709a62549c58e20af8a38bde1c3
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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