Butylamine → HCID 58900269, compound

HRID 642640Notes

Reaction equation

HRID 642640 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=1)[C:6]1[C:22](=[O:27])[O:23][C:24](=[O:26])[CH2:25][C:5]2=1.[CH2:28]([NH2:32])[CH2:29][CH2:30][CH3:31]>C(Cl)Cl>[CH2:28]([NH:32][C:24]([CH2:25][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[N:7]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:6]=1[C:22]([OH:23])=[O:27])=[O:26])[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 86613188HCID 86613188, compound

Product 1

HCID 58900269HCID 58900269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-fluoro-9-naphthalen-1-ylmethyl-4,9-dihydro-pyrano[3,4-b]indole-1,3-dione (1.0 mmole) in CH2Cl2 (3 ml) was added n-butylamine (5 mmole) and stirring was continued at 60° C. until completion of the reaction. The mixture was evaporated and the residue partitioned between aqueous HCl and AcOEt. The organic layer was dried, evaporated and the residue triturated with diethylether to give 3-butylcarbamoylmethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid as a white solid. MS: 431.4 ([M−H]−).

Workup

  1. customwas continued at 60° C. until completion of the reaction
  2. customThe mixture was evaporated
  3. customthe residue partitioned between aqueous HCl and AcOEt
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe residue triturated with diethylether

Sources & evidence

ORD record
ord-719c597693b943aea7207e01a2dec6d4
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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