Cis tert-Butyl 4-aminocyclohexylcarbamate → HCID 66818641, compound

HRID 1024733Notes

Reaction equation

[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[CH:17]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1)#[N:2].[C:29]([O:33][C:34](=[O:43])[NH:35][CH:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]1)([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34](=[O:43])[NH:35][CH:36]1[CH2:37][CH2:38][CH:39]([NH:42][C:12](=[O:14])[C:11]2[CH:15]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[CH:17]=[C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:28][CH:27]=3)[CH:10]=2)[CH2:40][CH2:41]1)([CH3:32])([CH3:30])[CH3:31]

Participants

Reactant 2

HCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

HCID 66818681HCID 66818681, compound

Product 1

HCID 66818641HCID 66818641, compoundYield 89.4%

Procedure

Following the procedure of Example 5(c) 3-(4-cyano benzyloxy)-5-(4-cyano phenoxy)benzoic acid 0.55 g (1.48 mmol) and (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.316 g, 1.48 mmol) were used to afford 0.75 g of the required product. 1H NMR (DMSO-d6): δ 1.25 (4H, m), 1.40 (9H, s), 1.8 (4H, m), 3.2 (1H, m), 3.7 (1H, m), 5.3 (2H, s), 6.74 (1H, d), 7.02 (1H, s), 7.1 (2H, s), 7.22 (1H, s), 7.44 (1H, s), 7.66 (2H, d), 7.88 (4H, m), 8.28 (1H, d).

Sources & evidence

ORD record: ord-2d233f4cf33d46afbba95d5cca6a59fa
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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