4-Pyridinemethanamine → HCID 68768913, compound

HRID 1173029Notes

Reaction equation

HRID 1173029 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=1)[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[CH2:21][C@H:20]2[C:22](O)=[O:23])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:52][CH2:53][C:54]1[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=1>ClCCl.CN(C=O)C>[C:2]1([O:1][C:8]2[CH:9]=[C:10]([CH2:11][NH:12][C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]4[CH2:21][C@H:20]4[C:22]([NH:52][CH2:53][C:54]4[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=4)=[O:23])=[CH:15][CH:14]=3)[CH:25]=[CH:26][CH:27]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 773174-PyridinemethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11739868HCID 11739868, compound

Product 1

HCID 68768913HCID 68768913, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of racemic-(trans)-2-{4-[(3-phenoxybenzyl)amino]phenyl}cyclopropanecarboxylic acid (I-2a) (0.10 g, 0.231 mmol) in dichloromethane (2 mL) and DMF (3 mL) was added HATU (0.27 g, 0.71 mmol). The mixture was stirred for 15 min followed by addition of 4-(aminomethyl)pyridine (0.10 g, 0.94 mmol). The solution stirred for 6 h after which the dichloromethane was removed via rotavap. Sat. NaHCO3 and ethyl acetate were added and the organic layer separated and washed with H2O, dried over MgSO4, filtered and concentrated. The resulting oil was triterated with Et2O and formed a cream ppt which was filtered and dried under high vacuum to give the title compound as a cream powder (0.08 g, 40%). 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=5.4 Hz, 2H), 7.34-7.28 (m, 3H), 7.26 (d, J=5.5 Hz, 2H), 7.11-7.07 (m, 2H), 7.01-6.99 (m, 3H), 6.92-6.90 (m, 3H), 6.55 (d, J=8.4 Hz, 2H), 6.01-5.98 (m, 1H), 4.50-4.47 (m, 2H), 4.29 (s, 2H), 4.03 (s, 1H), 2.48-2.43 (m, 1H), 1.58-1.51 (m, 1H), 1.24-1.19 (m, 2H). ES-MS m/z 450 (MH+).

Workup

  1. customwas removed via rotavap
  2. additionSat. NaHCO3 and ethyl acetate were added
  3. customthe organic layer separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customformed a cream ppt which
  9. filtrationwas filtered
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-1f27f2473b5e45ef8c3b2097d8b0001c
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

Loading…