2-Propanamine, 1-methoxy-, (2S)- → HCID 118036484, compound

HRID 1777967Notes

Reaction equation

HRID 1777967 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH2:6])[CH3:5].[NH2:7][C:8]1[CH:15]=[C:14](F)[C:11]([C:12]#[N:13])=[CH:10][N:9]=1>CC(N(C)C)=O>[NH2:7][C:8]1[CH:15]=[C:14]([NH:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])[C:11]([C:12]#[N:13])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 70215362-Propanamine, 1-methoxy-, (2S)-HCID 1180369016-Amino-4-fluoronicotinonitrile2×

Product 1

HCID 118036484HCID 118036484, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (S)-1-methoxy-2-propylamine (5.91 g, 65.6 mmol), 6-amino-4-fluoronicotinonitrile (intermediate 21, 3.0 g, 21.88 mmol) and diidopropylethylamine (11.52 ml, 65.6 mmol) in DMA (50 ml) was heated at 60° C. in a septum sealed reaction vessel for 48 h. The reaction mixture partitioned between DCM and aqueous NH4Cl, extracted with DCM (3×), the combined organic extracts were dried over Na2SO4 and evaporated to give the title compound as a pale yellow oil. (UPLC-MS 7) tR 0.40; ESI-MS 207.1 [M+H]+.

Workup

  1. customsealed
  2. customreaction vessel for 48 h
  3. customThe reaction mixture partitioned between DCM and aqueous NH4Cl
  4. extractionextracted with DCM (3×)
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-e991815ded9445c8abcd45df82c40048
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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