Ethyl chloroformate → HCID 66818666, compound

HRID 1024815Notes

Reaction equation

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

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 66818786HCID 66818786, compound

Product 1

HCID 66818666HCID 66818666, compoundYield 68.7%

Procedure

Following procedure of Example 11(e) 3,5-bis-(4-cyano-phenoxy)-N-piperidin-4-yl-benzamide 0.5 g (1.14 mmol) and ethyl choroformate (0.186 g, 1.71 mmol) were used to afford 0.4 g of the required product. 1H NMR (DMSO-d6): 81.21 (311, t), 1.42 (4H, m), 1.81 (3H, d), 2.92 (2H, m), 4.12 (2H, m), 7.26 (5H, d), 7.52 (2H, d), 7.92 (4H, d), 8.41 (1H, d).

Sources & evidence

ORD record: ord-2f64e4ab9eae462c9bb52b3d7abd27aa
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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