Cyclopropanemethanamine → HCID 57665462, compound

HRID 1173035Notes

Reaction equation

HRID 1173035 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]([OH:24])=O)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=[N:43][C:38]2[CH:39]=[CH:40][CH:41]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NCC1CC1>ClCCl.CN(C=O)C>[CH:39]1([CH2:38][NH:43][C:22]([CH:20]2[CH2:21][CH:19]2[C:16]2[CH:17]=[CH:18][C:13]([NH:12][CH2:11][C:10]3[CH:25]=[CH:26][CH:27]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)=[CH:14][CH:15]=2)=[O:24])[CH2:41][CH2:40]1

Participants

6

Reactant 3

HCID 75646CyclopropanemethanamineHCID 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 57665462HCID 57665462, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (+)-(trans)-2-{4-[(3-phenoxybenzyl)amino]phenyl}cyclopropanecarboxylic acid (III-3b) (0.09 g, 0.25 mmol) in dichloromethane (2 mL) and DMF (1 mL) was added HATU (0.14 g, 0.37 mmol). The mixture was stirred for 15 min followed by addition of aminomethylcyclopropane (0.03 g, 0.37 mmol). The solution stirred for 4 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 crude material was purified on silica gel eluting with an increasing gradient from hexanes to 30% ethyl acetate/hexanes to give the title compound as a white powder (0.01 g, 11%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.28 (m, 3H), 7.10-7.08 (m, 2H), 7.02-6.98 (m, 3H), 6.92-6.89 (m, 3H), 6.55 (d, J=8.3 Hz, 2H), 5.68 (s, 1H), 4.29 (s, 2H), 4.01 (s, 1H), 3.15-3.12 (m, 2H), 2.39 (s, 1H), 1.57-1.46 (m, 2H), 1.17-1.14 (m, 1H), 0.95 (s, 1H), 0.51 (d, J=7.7 Hz, 2H), 0.20 (d, J=4.6 Hz, 2H). ES-MS m/z 413.3 (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. customThe crude material was purified on silica gel eluting with an increasing gradient from hexanes to 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fd2e1a56c860468cb35a530d874eced2
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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