[3,5-Bis-(4-cyano-phenoxy)-phenyl]-amine → HCID 178453962, compound

HRID 1024798Notes

Reaction equation

HRID 1024798 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([C:20]1[CH:42]=[CH:41][C:23]([O:24][C:25]2[CH:26]=[C:27]([NH2:40])[CH:28]=[C:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)[CH:30]=2)=[CH:22][CH:21]=1)#[N:19]>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15](=[O:17])[NH:40][C:27]2[CH:28]=[C:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)[CH:30]=[C:25]([O:24][C:23]3[CH:41]=[CH:42][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)[CH:26]=2)[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 66818846[3,5-Bis-(4-cyano-phenoxy)-phenyl]-amineHCID 178453972HCID 178453972, compound

Product 1

HCID 178453962HCID 178453962, compoundYield 50.7%

Procedure

Following the procedure of Example 107(e) trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid 10.4 g (42.79 mmol) and [3,5-bis-(4-cyano-phenoxy)-phenyl]-amine (14.0 g, 42.79 mmol) were used to afford 12 g of the required product. 1H NMR (DMSO-d6): δ 1.2 (4H, m), 1.31 (9H, s), 1.8 (4H, d), 2.21 (1H, t), 3.1 (1H, m), 6.81 (1H, d), 7.04 (1H, s), 7.2 (6H, m) 7.91 (4H, dd), 10.0 (1H, s).

Sources & evidence

ORD record
ord-b04608eed80b444f8fcfd5629f96b2fb
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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