Benzene, 1-isocyanato-2-methoxy- → HCID 56670450, compound

HRID 1445718Notes

Reaction equation

HRID 1445718 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.[N:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])=[C:25]=[O:26].[N-]=C=O>O1CCCC1>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:24][C:25]([N:14]1[C@H:15]2[C:10]([C:9]3[CH:1]=[CH:2][CH:3]=[C:4]4[C:8]=3[C:7](=[CH:6][NH:5]4)[CH2:16]2)=[CH:11][C@@H:12]([C:17]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:18])[CH2:13]1)=[O:26]

Participants

5

Reactant 3

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 105034IsocyanateHCID 68543915HCID 68543915, compound

Product 1

HCID 56670450HCID 56670450, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.087 g (16.54 mmol) of the product of step 2 is dissolved in 80 ml tetrahydrofurane and 1.79 ml (16.5 mmol) 1-isocyanato-2-methoxy-benzene is added and stirred at room temperature. In order to trap excess isocyanate 0.3 equivalent 3-amino-1,2-propanediol is added and stirred for 2.5 hours. Then the reaction mixture is washed with saturated sodium hydrogen carbonate solution and brine, dried with Na2SO4 and partially evaporated. Crystallization give (6aR,9R)-9-(Pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid (2-methoxy-phenyl)-amide. MS/ES: 457 (M+H)+

Workup

  1. stirringstirred for 2.5 hours
  2. washThen the reaction mixture is washed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried with Na2SO4
  4. custompartially evaporated
  5. customCrystallization

Sources & evidence

ORD record
ord-e6c0d73cdedb427397741aaaf48ef46b
Source dataset
uspto-grants-2010_02
Patent number
US07666877B2

Reaction notes

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