Dichloromethane → HCID 66556279, compound

HRID 1629945Notes

Reaction equation

HRID 1629945 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]3[N:15]=[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[CH:13]=[N:12][CH:11]=3)[CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl:22]CCl>>[Cl:22][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]3[N:15]=[C:14]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[CH:13]=[N:12][CH:11]=3)[CH:9]=2)[NH:1][CH:2]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 66556278HCID 66556278, compound

Product 1

HCID 66556279HCID 66556279, compound

Procedure

To a solution of compound 4-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine (148) (40 mg, 0.142 mmol, 1.0 eq) in dichloromethane (6 mL) was added n-chlorosuccinamide (38 mg, 0.283 mmol, 2.0 eq) and the resulting reaction mixture was stirred at room temperature overnight. After completion of the reaction the solvents were removed and extracted into CH2Cl2. The organic layer was separated and the aqueous phase was extracted with CH2Cl2 to retain the crude material. The combined organic layer was washed with brine solution and dried over sodium sulphate and the solvents were removed by rotary evaporator. The crude material was purified by flash column with 100-200 mesh silica gel employing 70% EtOAc/hexane eluents to obtain the pure off-white colored solid of 4-(6-(3-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine 149 (10 mg). 1H NMR (400 MHz, CDCl3) δ: 9.0 (s, 1H), 8.83 (s, 1H), 8.52 (s, 1H), 8.45 (s, 1H), 8.10 (s, 1H), 7.34 (d, J=2.31 Hz, 1H), 3.89 (m, 4H), 3.70 (m, 4H); MS m/z 315.9 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. customAfter completion of the reaction the solvents
  3. customwere removed
  4. extractionextracted into CH2Cl2
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was extracted with CH2Cl2
  7. washThe combined organic layer was washed with brine solution
  8. dry with materialdried over sodium sulphate
  9. customthe solvents were removed by rotary evaporator
  10. customThe crude material was purified by flash column with 100-200 mesh silica gel employing 70% EtOAc/hexane eluents

Sources & evidence

ORD record
ord-03b52d9d869d44148730f204f95695f4
Source dataset
uspto-grants-2014_07
Patent number
US08791112B2

Reaction notes

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