N-Methylbenzylamine → HCID 59577482, compound

HRID 1947544Notes

Reaction equation

HRID 1947544 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:13]=[CH:14][C:15]2[O:19][C:18]([C:20](Cl)=[O:21])=[CH:17][C:16]=2[CH:23]=1.[CH2:24]([NH:31][CH3:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCN(CC)CC>C(Cl)Cl>[CH2:24]([N:31]([CH3:32])[C:20]([C:18]1[O:19][C:15]2[CH:14]=[CH:13][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:23][C:16]=2[CH:17]=1)=[O:21])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7669N-Methylbenzylamine2×HCID 8471TriethylamineHCID 86647609HCID 86647609, compound

Product 1

HCID 59577482HCID 59577482, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carbonyl chloride hydrochloride (150 mg, 0.43 mmol) in CH2Cl2 (4.3 mL) was added N-benzyl-N-methylamine (55 μL, 0.43 mmol) and Et3N (0.12 mL, 0.86 mmol). The reaction mixture was stirred (rt, 2 h) before additional N-benzyl-N-methylamine (55 μL, 0.43 mmol) was added. The mixture was concentrated and purified by reverse phase chromatography to provide the title product as an orange oil (27 mg, 15%). MS (ESI): mass calcd. for C23H17N3O3S, 415.10; m/z found, 416.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.60 (d, J=3.7, 1H), 8.09 (dd, J=7.9, 1.5, 1H), 7.75 (br s, 1H), 7.66-7.49 (m, 1H), 7.46-7.28 (m, 8H), 5.05-4.62 (m, 2H), 3.45-2.94 (m, 3H).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-7b369923aeee493dabfca5885f70e373
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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