1,4-Dioxane hydrochloride → HCID 118590369, compound

HRID 1054475Notes

Reaction equation

HRID 1054475 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]([C:15]2[N:19]3[CH:20]=[C:21]([N:24]4[CH2:28][CH2:27][CH2:26][C@H:25]4[C:29]4[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=4[F:36])[CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[CH2:9]1)(C)(C)C.Cl.O1CCOCC1>O1CCOCC1>[NH2:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]([C:15]2[N:19]3[CH:20]=[C:21]([N:24]4[CH2:28][CH2:27][CH2:26][C@H:25]4[C:29]4[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=4[F:36])[CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[CH2:9]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131736338HCID 131736338, compound

Product 1

HCID 118590369HCID 118590369, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl((S)-1-(6-((S)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carbonyl)pyrrolidin-3-yl)carbamate (Isomer-II) (prepared by method similar to Example-1, employing (S)-tert-butyl pyrrolidin-3-ylcarbamate as amine followed by chiral separation in LUXAMYLOSE-2 column with eluent 1:1 Hexane:Ethanol isocratic solution) (0.16 g, 0.31 mmol), in Dioxane (2 mL), cooled to 5-10° C. was added Dioxane HCl (4 Molar) (2 mL) and stirred for 2 h at room temperature, after completion of reaction solvent was remove under vacuum and residue was dissolved in water and washed with diethylether and water was basified with sat.NaHCO3 (pH˜9) and solid was filter and dried to afford ((S)-3-aminopyrrolidin-1-yl)(6-((S)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridin-3-yl)methanone (0.07 g, 54.68% yield). MS (ESI): m/z 412.2 (M+H); 1H NMR (300 MHz, CDCl3) δ 8.66 (1H, bs), 7.98 (1H, bs), 7.54-7.51 (1H, d J=9 Hz), 7.31-7.29 (1H, m), 7.20-7.09 (1H, m), 6.94-6.91 (2H, m), 4.99-4.96 (1H, d J=9 Hz), 3.95-3.50 (4H, m), 2.19-1.80 (5H, m), 1.99 (1H, bs) ppm.

Workup

  1. customafter completion of reaction solvent
  2. customwas remove under vacuum and residue
  3. dissolutionwas dissolved in water
  4. washwashed with diethylether and water
  5. filtrationNaHCO3 (pH˜9) and solid was filter
  6. customdried

Sources & evidence

ORD record
ord-0ca5b3e85de249c4a02c42800106d4f3
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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