Triethylamine → HCID 10075053, compound

HRID 1677002Notes

Reaction equation

HRID 1677002 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH2:20])=[O:19])(=[O:7])=[O:6].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1.C(N(CC)CC)C.[N-]=C=O>ClCCl.CCOC(C)=O>[Br:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:18]([NH2:20])=[O:19])=[C:8]2[S:5]([NH:4][CH2:3][CH2:2][NH:1][C:30]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=1)=[O:31])(=[O:6])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 794431-Isocyanato-4-methoxybenzeneHCID 105034IsocyanateHCID 10248012HCID 10248012, compound

Product 1

HCID 10075053HCID 10075053, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 63 (50 mg) was combined with 4-methoxyphenyl isocyanate (21 mg) and triethylamine (58 μL) in 2 mL of dichloromethane and stirred at room temperature for 3 hours. An additional 18 μL of the isocyanate were added and the reaction stirred for 3 hours more, then diluted with EtOAc and washed with saturated NaHCO3 and brine. The solution was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by preparative reversed-phase HPLC followed by triteration with Et2O/hexane to give the titled product. ESI+ MS: 510 [M+H]+

Workup

  1. stirringthe reaction stirred for 3 hours more
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-096b24fadab346dca7fee31d316c9f4a
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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