HCID 66815771, compound → HCID 10379416, compound

HRID 1944545Notes

Reaction equation

HRID 1944545 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:29])[NH:18][C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.O.ClCCl>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][CH2:9][CH2:10]3)=[O:29])[CH:20]=1

Participants

5

Reactant 1

HCID 66815771HCID 66815771, compound

Product 1

HCID 10379416HCID 10379416, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(Quinolin-3-ylcarbamoyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1.4 g, 3.59 mmol) in trifluoroacetic acid (9 mL), water (1 mL) and dichloromethane (20 mL) was stirred at room temperature for 18 hours. The solvents were evaporated in vacuo and the residue was triturated in aqueous sodium bicarbonate. The product was collected by filtration and washed with water, to give an off white solid 1.03 g (99%). MS: m/z 290 (MH+). 1H NMR (DMSO-d6): δ 3.02 (t, 2 H), 3.56 (t, 2 H), 6.27 (br s, 1 H), 6.54 (d, 1 H), 7.56 (t, 1 H), 7.64 (t, 1 H), 7.71-7.76 (m, 2 H), 7.94 (m, 2 H), 8.82 (d, 1 H), 9.14 (d, 1 H) and 10.23 (s, 1 H).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was triturated in aqueous sodium bicarbonate
  3. filtrationThe product was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-6766f5b77c434dda978e7ede7aac0233
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…