5-Chloro-2-nitropyridine → HCID 66818537, compound

HRID 1024760Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:35]1[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[N:39][CH:40]=1>>[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([O:22][C:35]3[CH:40]=[N:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=3)[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 2598065-Chloro-2-nitropyridine

HCID 66818660HCID 66818660, compound

Product 1

HCID 66818537HCID 66818537, compoundYield 78.9%

Procedure

Following the procedure of Example 69(b) {4-[3-(4-cyanophenoxy)-5-hydroxy-benzoylamino]cyclohexyl}carbamic acid tert-butyl ester 1.2 g (2.65 mmol) and 5-chloro-2-nitro-pyridine (0.84 g, 5.31 mmol) were used to afford 1.2 g of the required product. 1H NMR (DMSO-d6): δ 1.28 (3H, m), 1.4 (10H, s), 1.8 (5H, m), 3.20 (1H, m), 3.7 (1H, m), 6.75 (1H, d), 7.25 (2H, d), 7.35 (1H, d), 7.5 (2H, s), 7.8 (1H, dd), 7.9 (2H, d), 8.35 (2H, d), 8.5 (1H, s).

Sources & evidence

ORD record: ord-f3f62997611f4b9984c8f1ecd15cc05b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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