Triethylamine → HCID 68777299, compound

HRID 1628542Notes

Reaction equation

HRID 1628542 reaction equation
[NH2:1][C:2]1[C:3]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])=[C:4]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=S)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1>[NH2:1][C:2]1[C:3]2[N:21]([CH2:22][CH2:23][CH2:24][OH:25])[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])=[N:9][C:4]=2[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632905HCID 86632905, compound

Product 1

HCID 68777299HCID 68777299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-{3-amino-5-fluoro-2-[(3-hydroxypropyl)amino]phenyl}-3-(2,4-dichlorophenyl)thiourea (1.95 g, 4.84 mmol), triethylamine (743 μL, 5.32 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (974 mg, 5.08 mmol) in tetrahydrofuran (25 mL) was stirred at 50° C. for 2 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (1.64 g, 4.43 mmol, 92%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-a0baaf8df2c644b8867c3710f5069a71
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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