Stannous chloride dihydrate → HCID 67022040, compound

HRID 404485Notes

Reaction equation

HRID 404485 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([N:16]3[CH2:21][CH2:20][S:19][CH2:18][CH2:17]3)[N:13]=[C:12]([N:22]3[CH:27]4[CH2:28][CH2:29][CH:23]3[CH2:24][O:25][CH2:26]4)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>N1C=CC=CC=1.CN(C=O)C>[CH:23]12[N:22]([C:12]3[N:13]=[C:14]([N:16]4[CH2:17][CH2:18][S:19][CH2:20][CH2:21]4)[N:15]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=4)[N:11]=3)[CH:27]([CH2:28][CH2:29]1)[CH2:26][O:25][CH2:24]2

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrate2×HCID 67022021HCID 67022021, compound

Product 1

HCID 67022040HCID 67022040, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 8-(4-(4-nitrophenyl)-6-thiomorpholino-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (0.418 g, 1.01 mmol) in pyridine (3 ml) and DMF (6 ml) was prepared. Tin(II) chloride dihydrate (0.569 g, 2.52 mmol) was then added and the off-white suspension was allowed to stir at room temperature for 16 hours, at which time the suspension was light yellow. The suspension was filtered, washing with methanol, and concentrated. LCMS indicated reaction had not gone to completion. The crude product was dissolved in DMF (6 ml) and pyridine (3 ml) and additional tin(II) chloride dihydrate (0.569 g, 2.52 mmol) was added. The solution was allowed to stir at room temperature for 18 hours, then filtered. The precipitate was washed with methanol and the filtrate was concentrated to provide 4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-thiomorpholino-1,3,5-triazin-2-yl)aniline (0.195 g, 50%) as a yellow solid. (M+H) 385.1.

Workup

  1. customwas prepared
  2. filtrationThe suspension was filtered
  3. washwashing with methanol
  4. concentrationconcentrated
  5. customreaction
  6. stirringto stir at room temperature for 18 hours
  7. filtrationfiltered
  8. washThe precipitate was washed with methanol
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4a540c20882f401dbbf3f1217c4e013e
Source dataset
uspto-grants-2014_06
Patent number
US08748421B2

Reaction notes

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