Sodium Carbonate → HCID 86345607, compound

HRID 1772654Notes

Reaction equation

HRID 1772654 reaction equation
C(O[C:6]([N:8]1[CH2:11][CH:10]([C:12]2[N:13]=[C:14]3[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[N:18][CH:17]=[C:16]([C:26]4[CH:27]=[CH:28][C:29]([N:32]5[CH2:37][CH2:36][N:35]([C:38]([O:40][CH2:41][C:42]6[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=6)=[O:39])[CH2:34][CH2:33]5)=[N:30][CH:31]=4)[N:15]3[CH:48]=2)[CH2:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].ClC1[CH:65]=[CH:64][C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[N:57]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.O>[O:23]1[CH2:24][CH2:25][N:20]([C:19]2[C:14]3[N:15]([CH:48]=[C:12]([CH:10]4[CH2:9][N:8]([C:6]5[CH:65]=[CH:64][C:63]6[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=6)[N:57]=5)[CH2:11]4)[N:13]=3)[C:16]([C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:37][CH2:36][N:35]([C:38]([O:40][CH2:41][C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)=[O:39])[CH2:34][CH2:33]4)=[N:30][CH:31]=3)=[CH:17][N:18]=2)[CH2:21][CH2:22]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 119282-ChloroquinolineHCID 117727918Benzyl 4-(5-(2-(1-(tert-butoxycarbonyl)azetidin-3-yl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86345607HCID 86345607, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of compound 29c (275 mg, 0.420 mmol) in DCM (3 mL), TFA (2 mL) was added. The resulting mixture was stirred at rt for 2 h and concentrated. The residue obtained was dried under reduced pressure overnight and re-dissolved in EtOH (5 mL). Na2CO3 (1.00 g, 9.50 mmol) and 2-chloroquinoline (234 mg, 1.43 mmol) were then added and the resulting mixture was heated at reflux for 5 h. The reaction mixture was allowed to cool to rt, diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:1-1:0 EtOA/heptane) to obtain compound 29d. Mass Spectrum (LCMS, ESI pos.) Calcd. for C39H39N9O3: 682.3 (M+H). Found 682.3.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customwas dried under reduced pressure overnight
  4. dissolutionre-dissolved in EtOH (5 mL)
  5. temperaturethe resulting mixture was heated
  6. temperatureat reflux for 5 h
  7. temperatureto cool to rt
  8. extractionextracted with EtOAc (3×20 mL)
  9. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue obtained
  13. customwas purified by flash column chromatography on silica gel (0:1-1:0 EtOA/heptane)

Sources & evidence

ORD record
ord-70e76a85dc6f42b0a615b9c2d0176ee5
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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