Methanol → HCID 178514106, compound

HRID 467546Notes

Reaction equation

HRID 467546 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([Br:23])[N:22]=2)=[O:17])[CH2:3]1.C[Si]([N:28]=[C:29]=[O:30])(C)C.C(N(CC)CC)C.CO>O1CCCC1>[NH2:28][C:29]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([Br:23])[N:22]=2)=[O:17])[CH2:3]1)=[O:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 178511726HCID 178511726, compound

Product 1

HCID 178514106HCID 178514106, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of imidazole 12 (29 mg, 0.076 mmol), trimethylsilyl isocyanate (18 mg, 0.15 mmol) and triethylamine (31 mg, 0.30 mmol) in tetrahydrofuran (1 mL) was stirred at r.t. for 4 h. Methanol (1 mL) was added and the mixture was stirred at r.t for 1 h. The solvents were removed in vacuo and chromatographic purification (ethyl acetate-hexane) of the residue gave urea 15 (21 mg, 64%) as a colorless oil. LCMS m/e (M+H+)=425.2.

Workup

  1. stirringthe mixture was stirred at r.t for 1 h
  2. customThe solvents were removed in vacuo and chromatographic purification (ethyl acetate-hexane) of the residue

Sources & evidence

ORD record
ord-faae9f2288e447c381349e11725bb843
Source dataset
uspto-grants-2014_01
Patent number
US08623857B2

Reaction notes

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