Triethylamine → t-Butyl N-{5-(3-dimethylaminophenoxy)-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl}-N-methylcarbamate

HRID 2303780Notes

Reaction equation

HRID 2303780 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]([CH3:17])[CH3:16])[CH:10]=2)=[CH:4][C:3]=1[N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].[O:27]=[C:28]1[NH:32][C:31](=[O:33])[CH:30]([CH2:34][C:35]2[CH:45]=[CH:44][C:38]([O:39][CH2:40][C:41](O)=[O:42])=[CH:37][CH:36]=2)[S:29]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>O1CCCC1>[CH3:17][N:15]([CH3:16])[C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:41](=[O:42])[CH2:40][O:39][C:38]2[CH:37]=[CH:36][C:35]([CH2:34][CH:30]3[S:29][C:28](=[O:27])[NH:32][C:31]3=[O:33])=[CH:45][CH:44]=2)=[C:3]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 18461351HCID 18461351, compound

Product 1

HCID 18461255t-Butyl N-{5-(3-dimethylaminophenoxy)-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl}-N-methylcarbamateYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to that described in Example (2-1), a reaction was carried out using t-butyl N-[2-amino-5-(3-dimethylaminophenoxy)phenyl]-N-methylcarbamate (1.00 g), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (1.57 g), diethyl cyanophosphonate (0.91 g), triethylamine (0.57 g) and anhydrous tetrahydrofuran (40 ml) and the reaction mixture was purified to give the desired product (1.69 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-00e66bc8bd304788aae7fe36a0ef9d91
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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