Oxalic acid dihydrate → Oxalic acid--3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}propyl benzoate (1/1)

HRID 1173781Notes

Reaction equation

HRID 1173781 reaction equation
O.O.[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[C:9]([O:17][CH2:18][CH2:19][CH2:20][N:21]1[C:29]2[C:24](=[CH:25][C:26]([CH2:32][C@H:33]([NH:35][CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[O:45][CH2:46][C:47]([F:50])([F:49])[F:48])[CH3:34])=[CH:27][C:28]=2[C:30]#[N:31])[CH2:23][CH2:22]1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(C)C>[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[C:9]([O:17][CH2:18][CH2:19][CH2:20][N:21]1[C:29]2[C:24](=[CH:25][C:26]([CH2:32][C@H:33]([NH:35][CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[O:45][CH2:46][C:47]([F:50])([F:49])[F:48])[CH3:34])=[CH:27][C:28]=2[C:30]#[N:31])[CH2:23][CH2:22]1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 532406151-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

Product 1

HCID 66713997Oxalic acid--3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}propyl benzoate (1/1)

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Isopropyl alcohol (50 mL) and oxalic acid dihydrate (1.20 g) were added to 3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}propyl benzoate (6.40 g) which was obtained in the Example 1, and the mixture was dissolved by heating. After seeding of the title compound, the mixture was stood overnight. The precipitated crystals were collected by filtration and washed with a small amount of cooled isopropyl alcohol and dried under vacuum to give 3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}propyl benzoate mono oxalate (5.43 g). At this time, the content of by-product (C-a) in the obtained product was 0.9%.

Workup

  1. customwas obtained in the Example 1
  2. dissolutionthe mixture was dissolved
  3. temperatureby heating

Sources & evidence

ORD record
ord-0dd83e6d13714d3f97e859e4800988c1
Source dataset
uspto-grants-2010_11
Patent number
US07834193B2

Reaction notes

Loading…