Triethylamine → HCID 10478660, compound

HRID 1768481Notes

Reaction equation

HRID 1768481 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[F:17])[CH2:7][N:6]1[C:18]([N:20]([CH3:22])[CH3:21])=[O:19].C[Si]([N:33]=[C:34]=[O:35])(C)C.C(N(CC)CC)C>C(Cl)Cl>[NH2:33][C:34]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[F:17])[CH2:7][N:6]1[C:18]([N:20]([CH3:22])[CH3:21])=[O:19])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 10001131HCID 10001131, compound

Product 1

HCID 10478660HCID 10478660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 20 mg (0.05 mmol) of amine 20-2 in CH2Cl2 was added a large excess of trimethylsilyl isocyanate and triethylamine. After stirring for 12 h, the reaction was partitioned between EtOAc and 10% KHSO4, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with MeOH/CHCl3 to provide 23-1 as a white solid. Data for 23-1: 1HNMR (500 MHz, d6-DMSO) δ 7.6 (m, 1H), 7.5-7.1 (m, 7H), 6.2 (s, 1H), 5.95 (m, 1H), 5.3 (s, 2H), 4.95 (m, 1H), 4.7 (m, 1H), 3.0 (m, 2H), 2.7 (s, 6H), 2.1 (m, 1H), 1.3 (m, 3H) ppm. HRMS (ES) calc'd M+H for C23H26ClFN4O2: 445.1801. Found: 445.1805.

Workup

  1. customthe reaction was partitioned between EtOAc and 10% KHSO4
  2. washthe organic phase was washed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by column chromatography on silica gel with MeOH/CHCl3

Sources & evidence

ORD record
ord-cbd2ee6b71ae470c8628c1bedd98edac
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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