Hydroxylamine → HCID 86607873, compound

HRID 736725Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@H:24]3[CH2:28][N:27]([CH2:29][C:30]#[CH:31])[CH2:26][C@H:25]3[C:32](OC(C)(C)C)=[O:33])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.FC(F)(F)C(O)=O.[NH2:46][OH:47]>>[OH:47][NH:46][C:32]([C@H:25]1[C@@H:24]([NH:23][S:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:19][CH:18]=2)(=[O:22])=[O:21])[CH2:28][N:27]([CH2:29][C:30]#[CH:31])[CH2:26]1)=[O:33]

Participants

Reactant 3

HCID 787Hydroxylamine

HCID 6422Trifluoroacetic acid

HCID 86607872HCID 86607872, compound

Product 1

HCID 86607873HCID 86607873, compoundYield 54%

Procedure

According to the procedure of Example 17, Steps 4 and 5, 117 mg of tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-prop-2-yn-1-ylpyrrolidine-3-carboxylate, was treated with trifluoroacetic acid, followed by the reaction with hydroxylamine to give 56 mg of cis-N-hydroxy-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-prop-2-yn-1-ylpyrrolidine-3-carboxamide in 54% yield. MS: 495 2(M+H)+

Sources & evidence

ORD record: ord-0bca501c61934ceab7903709947d09e1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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