Stannous chloride dihydrate → 5-Morpholinopyridin-2-amine

HRID 1366206Notes

Reaction equation

HRID 1366206 reaction equation
N1C=CC=CC=1C1N=NN(C2C=CC(NC3C4N(C=CN=4)C(C4C=CC(C(N)=O)=CC=4)=CN=3)=CC=2)C=1.[N+:37]([C:40]1[N:45]=[CH:44][C:43]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)=[CH:42][CH:41]=1)([O-])=O.O.O.[Sn](Cl)Cl>CO.Cl>[N:46]1([C:43]2[CH:42]=[CH:41][C:40]([NH2:37])=[N:45][CH:44]=2)[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 29279734-(6-Nitropyridin-3-yl)morpholineHCID 177573324-{8-[4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide

Product 1

HCID 113673465-Morpholinopyridin-2-amineYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In the same way as described in for Compound 154, step 2 using 4-(6-nitro-pyridin-3-yl)-morpholine (2.39 g, 11.43 mmol), tin(II) chloride dihydrate (12.9 g, 57.17 mmol) in MeOH (40 mL) and conc. HCl (12.4 mL). The reaction mixture is concentrated in vacuo cooled to 0° C. and dissolved in water. The aqueous solution is basified using conc. NaOH and extracted with ethyl acetate (3×). The organic layers are combined, dried over MgSO4, filtered and concentrated to afford the title compound (1.77 g, 87%) which is used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3d3ad81974fa4d4390cba3d02e5ea22e
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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