Boron trifluoride etherate → HCID 17894960, compound

HRID 2393151Notes

Reaction equation

HRID 2393151 reaction equation
[Cl:1][C:2]1C(C)=[N:4][O:5][C:6]=1[N:7]([CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1OC(=O)C)(=[O:10])=[O:9].C([SiH]([CH2:47][CH3:48])CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[Cl:1][C:2]1[C:47]([CH3:48])=[N:4][O:5][C:6]=1[N:7]([CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH2:20][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][CH:30]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18614038N-(4-chloro-3-methyl-5-isoxazolyi)-N-(methoxyethoxymethyl)-2-(alpha-acetoxynaphthylmethyl)thieno[2,3-b]pyridine-3-sulfonamide

Product 1

HCID 17894960HCID 17894960, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the method of Example 5(A) using N-(4-chloro-3-methyl-5-isoxazolyi)-N-(methoxyethoxymethyl)-2-(α-acetoxynaphthylmethyl)thieno[2,3-b]pyridine-3-sulfonamide (97 mg, 0.16 mmoles), CH2Cl2 (3 ml), triethylsilane (0.25 ml, 1.6 mmoles) and boron trifluoride etherate (0.19 ml, 1.6 mmoles). Flash chromatography (40% EtOAc/hexanes) provided 58 mg (66%) of the title compound as a yellow solid.

Workup

  1. customThe title compound was prepared by the method of Example 5(A)

Sources & evidence

ORD record
ord-e97c22f4e4e146a483d5c25d4d7ab27e
Source dataset
uspto-grants-1998_09
Patent number
US05804585

Reaction notes

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