Trifluoroacetic acid methylene chloride → (5)-1-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)benzoyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid salt

HRID 1772625Notes

Reaction equation

HRID 1772625 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:33]=[C:34]([CH2:36][CH2:37][C:38]4[CH:47]=[CH:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]=4)[N:35]=3)[C:10]([C:13]3[CH:32]=[CH:31][C:16]([C:17]([N:19]4[CH2:23][CH2:22][CH2:21][C@H:20]4[C:24]([O:26]C(C)(C)C)=[O:25])=[O:18])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49].C(Cl)Cl>>[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[N:9]([CH:33]=[C:34]([CH2:36][CH2:37][C:38]4[CH:47]=[CH:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]=4)[N:35]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:17]([N:19]4[CH2:23][CH2:22][CH2:21][C@H:20]4[C:24]([OH:26])=[O:25])=[O:18])=[CH:31][CH:32]=3)=[CH:11][N:12]=2)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86345488(S)-tert-Butyl 1-(4-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)benzoyl)pyrrolidine-2-carboxylate

Product 1

HCID 117728283(5)-1-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)benzoyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid saltYield 30%

Procedure

A solution of compound 17b (350 mg, 0.550 mmol) in TFA/DCM (10 mL, 1:4 v/v) was stirred at rt for 3 h. Solvent was evaporated and Et2O (30 mL) was added. The resulting solids were collected by filtration and washed with Et2O to obtain the title compound 35 as a yellow solid (142 mg, 30% yield). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 9.01 (d, J=8.8 Hz, 1H), 8.31 (d, J=8.0 Hz, 1H), 8.16-8.09 (m, 2H), 8.02 (d, J=8.8 Hz, 1H), 7.94-7.90 (m, 1H), 7.80 (s, 1H), 7.72-7.53 (m, 4H), 7.38-7.34 (m, 1H), 4.44-4.35 (m, 1H), 3.81-3.73 (m, 4H), 3.61-3.50 (m, 4H), 3.45-3.31 (m, 6H), 2.43-2.28 (m, 1H), 1.90-1.78 (s, 3H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C33H32N6O4: 577.2 (M+H). Found 577.1.

Workup

  1. customSolvent was evaporated
  2. additionEt2O (30 mL) was added
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-08f92228e396457aa79da3d9f13d174a
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…