Trifluoroacetic acid → HCID 18772069, compound

HRID 479695Notes

Reaction equation

HRID 479695 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:32])[NH:12][C:13]2[N:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24]C(=O)OC(C)(C)C)=[CH:20][CH:19]=3)[S:16][CH:17]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].C1(SC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[S:16][CH:17]=[C:13]([NH:12][C:11]([NH:10][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[N:9]=3)=[O:32])[N:14]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 59110551HCID 59110551, compound

Product 1

HCID 18772069HCID 18772069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an oven-dried, 25-mL, round-bottomed flask were placed N-[6-propylpyridine]-N′-[4-[N-Bocamino]pheny]-4-thiazolyl]urea (55 mg, 0.12 mmol, Example 187), thioanisole (0.35 mL) in CH2Cl2 (10 mL). TFA (0.35 mL) was added, the mixture was stirred at RT for 6 h then concentrated in vacuo. Purification by flash chromatography on silica gel [EtOAc/hexane (extracted with aq. NH4OH), 40:60] afforded the title compound. MS m/z: 354.0 (M+H). Calc'd for C18H19N50S: 353.13.

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification by flash chromatography on silica gel [EtOAc/hexane (extracted with aq. NH4OH), 40:60]

Sources & evidence

ORD record
ord-237a5d04e8b1490b9e55739688ce831f
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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