Triethylamine → HCID 76390342, compound

HRID 1445720Notes

Reaction equation

HRID 1445720 reaction equation
[CH:1]1[C:9]2[C:10]3[C@@H:15]([CH2:16][C:7]4[C:8]=2[C:4]([NH:5][CH:6]=4)=[CH:3][CH:2]=1)[NH:14][CH2:13][C@H:12]([C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18])[CH:11]=3.C([N:26]([CH2:29][CH3:30])[CH2:27]C)C.ClC(OC(Cl)(Cl)Cl)=[O:33].[F:39][C:40]1[CH:46]=CC=[CH:43][C:41]=1N>ClCCl>[F:39][C:40]1[CH:46]=[C:29]([NH:26][C:27]([N:14]2[CH:15]3[C:10]([C:9]4[CH:1]=[CH:2][CH:3]=[C:4]5[C:8]=4[C:7](=[CH:6][NH:5]5)[CH2:16]3)=[CH:11][CH:12]([C:17]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[O:18])[CH2:13]2)=[O:33])[CH:30]=[CH:43][CH:41]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 95842-FluoroanilineHCID 10426DiphosgeneHCID 68543915HCID 68543915, compound

Product 1

HCID 76390342HCID 76390342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

62 mg (0.20 mmol) of the product of step 2 of Example 45 is dissolved in 3 ml of dichloromethane and 0.14 ml (10 eq.) of triethylamine is added and 0.042 ml trichloromethyl chloroformate in 2 ml of dichloromethane. After 30 minutes at room temperature 0.14 ml of triethylamine (10 eq.) and 0.040 ml (2 eq.) of 2-fluoroaniline are added. After stirring for 22 hours at room temperature the reaction mixture is separated between 100 ml dichloro-methane and saturated sodium hydrogen carbonate solution. The organic layer is dried with Na2SO4 and evaporated. The crude product is purified by chromatography on silica gel eluting with ethyl acetate/cyclohexane 3:1 to give 6aR,9R)-9-(Pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid (3-fluoro-phenyl)-amide. MS/ES: 445 (M+H)+

Workup

  1. customis separated between 100 ml dichloro-methane and saturated sodium hydrogen carbonate solution
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customevaporated
  4. customThe crude product is purified by chromatography on silica gel eluting with ethyl acetate/cyclohexane 3:1

Sources & evidence

ORD record
ord-9dabd75a1c934730bf34ae6e7e3b039c
Source dataset
uspto-grants-2010_02
Patent number
US07666877B2

Reaction notes

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