Methylamine → HCID 90408407, compound

HRID 594038Notes

Reaction equation

HRID 594038 reaction equation
[CH3:1][NH2:2].CC1C=CC(S(O[CH2:14][C@H:15]2[O:20][CH2:19][CH2:18][N:17]([C:21]3[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][N:22]=3)[CH2:16]2)(=O)=O)=CC=1>CO>[Br:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([N:17]2[CH2:18][CH2:19][O:20][C@H:15]([CH2:14][NH:2][CH3:1])[CH2:16]2)[CH:26]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 90409573HCID 90409573, compound

Product 1

HCID 90408407HCID 90408407, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 2 M solution of methylamine in methanol was added (S)-(4-(4-bromopyridin-2-yl)morpholin-2-yl)methyl 4-methylbenzenesulfonate (1.0 eq). This solution was microwave heated at 80° C. After 1 h the solution was then concentrated in vacuo and water was added. The resulting suspension was sonicated and centrifuged. The water soluble portion was separated from the solids. The resulting aqueous solution of (R)-1-(4-(4-bromopyridin-2-yl)morpholin-2-yl)-N-methylmethanamine was used in the next step without further purification. LCMS (m/z) (M+H)=286.0/288.0, Rt=0.34 min.

Workup

  1. concentrationAfter 1 h the solution was then concentrated in vacuo and water
  2. additionwas added
  3. customThe resulting suspension was sonicated
  4. customThe water soluble portion was separated from the solids
  5. customThe resulting aqueous solution of (R)-1-(4-(4-bromopyridin-2-yl)morpholin-2-yl)-N-methylmethanamine was used in the next step without further purification

Sources & evidence

ORD record
ord-e14b19294da74389b8ce128879895998
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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