3-Pentanamine → HCID 68680738, compound

HRID 1174619Notes

Reaction equation

HRID 1174619 reaction equation
[NH2:1][CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4].[CH:7]1([NH:10][C:11]([C:13]2[CH:14]=[C:15]([F:29])[C:16]([CH3:28])=[C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][N:20]=3)[CH:18]=2)=[O:12])[CH2:9][CH2:8]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:7]1([NH:10][C:11]([C:13]2[CH:14]=[C:15]([F:29])[C:16]([CH3:28])=[C:17]([C:19]3[N:20]=[CH:21][C:22]([C:23]([NH:1][CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4])=[O:25])=[CH:26][CH:27]=3)[CH:18]=2)=[O:12])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 120193-PentanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21914626HCID 21914626, compound2×

Product 1

HCID 68680738HCID 68680738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Aminopentane (147 μl) in DMF (8 ml) was added to a mixture of 6-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}nicotinic acid (Intermediate 8, 200 mg), HATU (228 mg) and DIPEA (348 μl) in DMF (8 ml) and the reaction stirred for 18 hours at room temperature. The DMF was evaporated under vacuum and the residue dissolved in ethyl acetate and applied to an SCX SPE (10 g). The SPE was washed with ethyl acetate then methanol/ethylacetate (1:9) and the product elutes with 0.880 ammonia/methanol/ethyl acetate (1:1:8). The product fraction was reduced to dryness under vacuum and purified on a silica SPE (500 mg) eluting with an ethyl acetate/cyclohexane gradient to give after evaporation of the solvents 6-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}-N-(1-ethylpropyl)-3-pyridinecarboxamide.

Workup

  1. customThe DMF was evaporated under vacuum
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe SPE was washed with ethyl acetate
  4. custompurified on a silica SPE (500 mg)
  5. washeluting with an ethyl acetate/cyclohexane gradient
  6. customto give
  7. customafter evaporation of the solvents 6-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}-N-(1-ethylpropyl)-3-pyridinecarboxamide

Sources & evidence

ORD record
ord-f438ab2aba46427499865314490ee5e7
Source dataset
uspto-grants-2010_11
Patent number
US07838540B2

Reaction notes

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