Triethylamine → HCID 68656386, compound

HRID 2369102Notes

Reaction equation

HRID 2369102 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16]3[N:20]([C:21]4[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=4)[NH2:24])[N:19]=[C:18]([C:28]([F:31])([F:30])[F:29])[CH:17]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C[Si]([N:36]=[C:37]=[O:38])(C)C.C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.C1COCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16]3[N:20]([C:21]4[CH:22]=[C:23]([NH:24][C:37]([NH2:36])=[O:38])[CH:25]=[CH:26][CH:27]=4)[N:19]=[C:18]([C:28]([F:31])([F:29])[F:30])[CH:17]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 2724141Tetrabutylammonium FluorideHCID 59632423HCID 59632423, compound

Product 1

HCID 68656386HCID 68656386, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the 3-(5-(5-(3-(methylsulfonyl)phenyl)-thiophen-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)aniline in anhydrous DCM (1.0 mL) and THF (3.0 mL) was added trimethylsilyl isocyanate (112 mg, 0.85 mmol) and triethyl amine (29 mg, 0.28 mmol). The reaction mixture was stirred under nitrogen atmosphere for overnight. A 1.0 M solution of tetra-butylammonium fluoride (1.42 mL, 1.42 mmol) in THF was added and the mixture was stirred at room temperature for overnight. The solvent was evaporated in vacuo and the resulting residue was purified by HPLC, providing the urea product (70 mg, 49%). 1H-NMR (Acetone-d6): δ 8.56 (s, 1H), 8.13 (m, 1H), 7.98 (m, 1H), 7.91 (m, 1H), 7.69 (m, 1H), 7.60 (m, 1H), 7.49 (m, 1H), 7.20 (m, 1H), 7.17 (m, 1H), 6.44 (br, 2H), 3.18 (s, 3H). MS (ES): 507 [M+H]+.

Workup

  1. stirringthe mixture was stirred at room temperature for overnight
  2. customThe solvent was evaporated in vacuo
  3. customthe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-0258b8eb9a114046b43070fa2ef462d2
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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