Diisopropylethylamine → [5-(5-Bromo-6-chloro-pyridine-3-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester

HRID 1696879Notes

Reaction equation

HRID 1696879 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH2:19])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Br:30][C:31]1[CH:32]=[C:33]([S:38](Cl)(=[O:40])=[O:39])[CH:34]=[N:35][C:36]=1[Cl:37]>>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:19][S:38]([C:33]3[CH:34]=[N:35][C:36]([Cl:37])=[C:31]([Br:30])[CH:32]=3)(=[O:40])=[O:39])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chlorideHCID 59192558(5-Amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

Product 1

HCID 59192603[5-(5-Bromo-6-chloro-pyridine-3-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl esterYield 55%

Procedure

Starting with (5-amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (example 1-1, method A, 3rd step) (2.0 g, 7.2 mmol), diisopropylethylamine (2.0 g, 15.5 mmol) and 5-bromo-6-chloro-pyridine-3-sulfonyl chloride (2.1 g, 7.3 mmol), using the method analogous to the one for example 1-1, method A, 4th step, [5-(5-bromo-6-chloro-pyridine-3-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester (2.1 g, 55%) was obtained. MS cald. for C21H24BrClN2O5S 530, obsd. 531 [(M+H)+].

Sources & evidence

ORD record
ord-76be4536979945f081469d8131e06363
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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