Ethylenediamine → (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid ethylenediamine salt hydrate

HRID 1526423Notes

Reaction equation

HRID 1526423 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12.[CH2:34]([NH2:37])[CH2:35][NH2:36].C(#N)C>C1COCC1>[OH2:11].[CH2:34]([NH2:37])[CH2:35][NH2:36].[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6342AcetonitrileHCID 53362086(R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

Product 1

HCID 131733173(R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid ethylenediamine salt hydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-2-(9-Chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (15 mg) was dissolved in THF (0.5 mL) and aqueous ethylenediamine (16 uL, 2.27 M) was added. The homogeneous solution was left to stir at room temperature for 2d. ACN (300 μL) was then added and the reaction was stirred at room temperature for one additional day. The reaction mixture was evaporated to dryness and 0.5 mL of EtOAc was added. After stiffing for 24 h at room temperature, a solid had formed which was collected by filtration. The PXRD pattern of the title compound is shown in FIG. 10; and the DSC and TGA are shown in FIG. 11.

Workup

  1. waitThe homogeneous solution was left
  2. customThe reaction mixture was evaporated to dryness and 0.5 mL of EtOAc
  3. additionwas added
  4. customa solid had formed which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-573e21a452624ed8acf5f1575512fa33
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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