Trifluoroacetic acid → HCID 25050873, compound

HRID 1020250Notes

Reaction equation

HRID 1020250 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9](CC2C=CC(OC)=CC=2OC)[C:10]([NH:12][C:13]2[S:14][CH:15]=[C:16]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[N:17]=2)=[O:11])[S:5][C:6]=1[Br:7].C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10]([NH:12][C:13]2[S:14][CH:15]=[C:16]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[N:17]=2)=[O:11])[S:5][C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86622751HCID 86622751, compound

Product 1

HCID 25050873HCID 25050873, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Deprotection: The 1-(4,5-Dibromo-thiophen-2-ylmethyl)-1-(2,4-dimethoxy-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea was treated with TFA followed by the addition of a drop of anisole and a drop of water. Stirred overnight at ambient temperature. The volatiles were removed in vacuo and the crude material was purified by taking up in MeOH and filtering to remove insolubles. The filtrate was concentrated in vacuo, and the resulting solid titrated with ether to give the title compound. 1H NMR (400 MHz, DMSO): 10.70 (br s, 1H), 7.17 (br m, 1H), 7.00 (s, 1H), 6.88 (s, 1H), 4.42 (d, 2H), 4.37 (s, 2H), 3.55 (m, 2H), 3.45 (m, 2H), 3.24 (s, 3H). MS (ES+): M/Z 484, 486 and 488 (M+1).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude material was purified
  3. filtrationfiltering
  4. customto remove insolubles
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d80f64f82d8142f887ff464e1b22859b
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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