Triethylamine → HCID 59577635, compound

HRID 1947546Notes

Reaction equation

HRID 1947546 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:22]=[CH:21][C:15]2[C:16]([CH2:19][NH2:20])=[CH:17][O:18][C:14]=2[CH:13]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](Cl)=[O:32])=[CH:26][CH:25]=1.CCN(CC)CC>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([NH:20][CH2:19][C:16]2[C:15]3[CH:21]=[CH:22][C:12]([O:11][C:3]4[S:2][C:10]5[C:5]([N:4]=4)=[N:6][CH:7]=[CH:8][CH:9]=5)=[CH:13][C:14]=3[O:18][CH:17]=2)=[O:32])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 906924-Chlorophenylacetyl chloride3×HCID 66786500HCID 66786500, compound

Product 1

HCID 59577635HCID 59577635, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To C-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-yl]-methylamine hydrochloride (100 mg, 0.30 mmol) in DCM (3 mL) was added 4-chlorophenylacetyl chloride (57 mg, 0.30 mmol) and Et3N (0.13 mL, 0.90 mmol). The reaction mixture was stirred (rt, 16 h). Another equivalent of 4-chlorophenylacetyl chloride (57 mg, 0.30 mmol) was added, but the reaction remained at 50% conversion. Two equivalents of 4-chlorophenylacetyl chloride (114 mg, 0.60 mmol) and three equivalents of Et3N (0.13 mL, 0.90 mmol) were added. Upon reaction completion, the mixture was washed with sat'd. aq. NaHCO3 and extracted with DCM. After drying and concentration, the residue was purified by reverse phase HPLC to provide the title compound (47 mg, 35%). MS (ESI): mass calcd. for C23H16ClN3O3S, 449.06; m/z found, 449.9 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.56 (dd, J=4.8, 1.6, 1H), 8.04 (dd, J=7.9, 1.6, 1H), 7.60 (d, J=2.0, 1H), 7.58-7.53 (m, 2H), 7.33-7.29 (m, 2H), 7.28-7.24 (m, 1H), 7.24-7.18 (m, 3H), 5.70 (s, 1H), 4.55 (d, J=5.8, 2H), 3.58 (s, 2H).

Workup

  1. customUpon reaction completion
  2. washthe mixture was washed with sat'd
  3. extractionaq. NaHCO3 and extracted with DCM
  4. customAfter drying
  5. concentrationconcentration
  6. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2a4b29f685384a24845c130db7404625
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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