Cyclopropylamine → N-Cyclopropyl-3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxamide

HRID 337597Notes

Reaction equation

HRID 337597 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:16]([OH:18])=O)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.C1(N)CC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CCOC(C)=O.CN(C=O)C>[CH:25]1([NH:21][C:16]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)=[O:18])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668958083-{[2-(Methyloxy)ethyl]amino}-1-naphthalenecarboxylic acid

Product 1

HCID 67062005N-Cyclopropyl-3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (0.1 M) solution of 3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxylic acid (1 eq.) from the previous step, Hunig's base (3 eq.) and cyclopropylamine (1.5 eq.) was added portionwise O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.2 eq.). The resulting reaction solution was stirred at RT for 48 h. The now reddish solution was diluted with EtOAc and washed sequentially with 1 N aq. NaOH, water and brine. The organic extract was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a white solid.

Workup

  1. customThe resulting reaction solution
  2. washwashed sequentially with 1 N aq. NaOH, water and brine
  3. extractionThe organic extract
  4. dry with materialwas then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto afford a brown oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-163f2557c0be437e847a7c78ea22af59
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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