Propylamine → HCID 68651738, compound

HRID 646726Notes

Reaction equation

HRID 646726 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19](S(C3C=CC([N+]([O-])=O)=CC=3[N+]([O-])=O)(=O)=O)[C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[CH:13]=2)=[CH:4][N:3]=1.C(N)CC>C(Cl)Cl.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[CH:13]=2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 7852PropylamineHCID 86607842HCID 86607842, compound

Product 1

HCID 68651738HCID 68651738, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-(3-{[[(2,4-dinitrophenyl)sulfonyl][(1S)-2,3-dihydro-1H-inden-1-yl]amino}methyl}phenyl]-N-methylpyridine-3-carboxamide was treated with excess n-propylamine (4 eq) in CH2Cl2 (150 mL). The mixture was diluted with additional ethyl acetate (200 mL). The mixture was subsequently washed with aqueous saturated sodium carbonate (3×30 mL) and brine (3×30 mL). The combined organic fractions were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by preparative HPLC (acetonitrile/water) gave desired product (5.8 g). The compound was converted to the hydrochloride salt using 4 M solution HCl in dioxane: 1H NMR (400 MHz; DMSO-d6): 9.9 (br s, NH); 9.02 (s, 1H); 8.9 (s, 1H); 8.6 (s, 1H); 8.35 (br s, NH); 8.2 (s, 1H); 7.8 (d, 2H); 7.75 (m, 2H); 7.37 (m, 2H1); 7.29 (m, 1H); 4.85 (m, 1H); 4.25 (m, 2H); 3.4 (m, 1H); 2.9 (m, 1H); 2.80 (d, 3H); 2.43 (m, 1H); 2.4 (m, 1H); MS (EI) for C23H24N4O HCl: 374 (MH+).

Workup

  1. washThe mixture was subsequently washed with aqueous saturated sodium carbonate (3×30 mL) and brine (3×30 mL)
  2. dry with materialThe combined organic fractions were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by preparative HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-8e825f579ee34d5fb2441886aa4fe214
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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