Cis tert-Butyl 4-aminocyclohexylcarbamate → (4-{[2,6-Bis-(4-cyano-phenoxy)pyridine-3-carbonyl]amino}-cyclohexyl)-carbamic Acid Tert-butyl Ester

HRID 1024682Notes

Reaction equation

HRID 1024682 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[N:16]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])=[CH:5][CH:4]=1)#[N:2].[C:28]([O:32][C:33](=[O:42])[NH:34][CH:35]1[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33](=[O:42])[NH:34][CH:35]1[CH2:36][CH2:37][CH:38]([NH:41][C:10]([C:9]2[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:27][CH:26]=3)=[N:16][C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[O:11])[CH2:39][CH2:40]1)([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 676059982,6-Bis(4-cyanophenoxy)-nicotinic acid

Product 1

HCID 66818602(4-{[2,6-Bis-(4-cyano-phenoxy)pyridine-3-carbonyl]amino}-cyclohexyl)-carbamic Acid Tert-butyl EsterYield 67.3%

Procedure

Following the procedure of Example 5(c) 2,6-bis(4-cyano phenoxy)-nicotinic acid 0.335 g (0.94 mmol) and (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.2 g, 0.94 mmol) were used to afford 0.35 g of the required product. Percentage purity (LCMS): 86.8%, (M+1)=553.6 (with BOC). 1H NMR (DMSO-d6): δ 1.25 (4H, m), 1.38 (9H, s), 1.82 (4H, m), 3.18 (1H, m), 3.64 (1H, m), 6.74 (1H, d), 6.95 (1H, d), 7.28 (4H, dd), 7.82 (4H, dd), 8.08 (1H, d), 8.21 (1H, d).

Sources & evidence

ORD record
ord-79052a6e4ae34591bb3b80964286d0e5
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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