5-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-isocyanato-4-methoxybenzonitrile → N,N'-Diisopropylethylenediamine

HRID 630421Notes

Reaction equation

HRID 630421 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([O:21][CH3:22])=[CH:12][C:13]([N:18]=[C:19]=[O:20])=[C:14]([CH:17]=1)[C:15]#[N:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:23][C:24]([C:41]1[S:42][CH:43]=[CH:44][CH:45]=1)([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)[C:25]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][CH3:35])[CH2:30][CH2:29]1)=[O:26]>>[Si:1]([O:8][CH2:9][C:10]1[C:11]([O:21][CH3:22])=[CH:12][C:13]([N:18]=[C:19]=[O:20])=[C:14]([CH:17]=1)[C:15]#[N:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3].[OH:23][C:24]([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)([C:41]1[S:42][CH:43]=[CH:44][CH:45]=1)[C:25]([O:27][C@H:28]1[CH2:29][CH2:30][C@H:31]([NH:34][CH3:35])[CH2:32][CH2:33]1)=[O:26].[CH:31]([NH:34][CH2:35][CH2:19][NH:18][CH:13]([CH3:12])[CH3:14])([CH3:32])[CH3:30]

Participants

5

Reactant 2

HCID 874113275-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-isocyanato-4-methoxybenzonitrileHCID 178484861HCID 178484861, compound

Product 3

HCID 77628N,N'-DiisopropylethylenediamineHCID 874113275-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-isocyanato-4-methoxybenzonitrileHCID 178484861HCID 178484861, compound

Procedure

Obtained as a yellow solid (14%) from 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-isocyanato-4-methoxybenzonitrile (intermediate 132; 0.48 g, 1.51 mmol), trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5, 0.44 g, 1.13 mmol) and diisopropylethylendiamine (0.6 mL, 3.44 mmol) following the experimental procedure as described in intermediate 61, followed by a purification by column chromatography with silica gel, eluting with methylen chloride/isopropanol (9:1).

Sources & evidence

ORD record
ord-a3d7467893134811bb54cd72167ca97a
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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