Triethylamine → HCID 58002127, compound

HRID 1642848Notes

Reaction equation

HRID 1642848 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)[CH2:16][NH:15][CH2:14]3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl:37][C:38](OC(Cl)(Cl)Cl)=[O:39]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:27])[F:28])=[CH:21][CH:20]=4)[CH2:16][N:15]([C:38]([Cl:37])=[O:39])[CH2:14]3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 58002164HCID 58002164, compound

Product 1

HCID 58002127HCID 58002127, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 1.00 g (2.46 mmol) of the compound from Example 178A and 0.34 ml (248 mg, 2.46 mmol) of triethylamine were initially charged in 167 ml of dichloromethane. 0.12 ml (242 mg, 1.23 mmol) of trichloromethyl chloroformate (diphosgene) was added dropwise. The reaction mixture was stirred at RT for 16 h, washed quickly with a little ice-water, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel. Yield: 944 mg (68% of theory, 83% of theory)

Workup

  1. washwashed quickly with a little ice-water
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d8f8eda10a89442db0b8c946c4400022
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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