Methylamine → HCID 11717666, compound

HRID 1869638Notes

Reaction equation

HRID 1869638 reaction equation
Cl.[CH:2]1([N:6]2[CH2:11][CH2:10][CH:9]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[CH:21][C:22]([C:25](Cl)=[O:26])=[N:23][CH:24]=4)[CH2:15][CH2:14]3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1.[CH3:28][NH2:29]>ClCCl.O1CCCC1>[CH:2]1([N:6]2[CH2:11][CH2:10][CH:9]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:29][CH3:28])=[O:26])=[N:23][CH:24]=4)[CH2:15][CH2:14]3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86620012HCID 86620012, compound

Product 1

HCID 11717666HCID 11717666, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-{4-[(1-Cyclobutyl-4-piperidinyl)methyl]-1-piperidinyl}-2-pyridinecarbonyl chloride hydrochloride (may be prepared as described in Example 11, step 1) was dissolved in dichloromethane (10 ml) and added dropwise to a stirred solution of methylamine (1.57 ml of a 2M solution in tetrahydrofuran) in dichloromethane (10 ml) cooled to 0° C. over 1 h. The reaction was allowed to stir for a further 3 h before the mixture was evaporated. Chromatography (silica gel, eluting with methanol/dichloromethane, 0-20%) afforded the title compound (E11) (0.13 g). MS electrospray (+ion) 371 (MH+).1H NMR δ (CDCl3): 8.14 (1H, d, J=2.8 Hz), 8.01 (1H, d, J=8.8 Hz), 7.75 (1H, m), 7.19 (1H, dd, J=2.8, 8.8 Hz), 3.80 (2H, m), 3.00 (4H, m), 2.82 (3H, m), 2.19-1.21 (21H, m obscured by H2O)

Workup

  1. customwas evaporated
  2. washChromatography (silica gel, eluting with methanol/dichloromethane, 0-20%)

Sources & evidence

ORD record
ord-1d89228b64ce4ef2bbadde1f8e4397cf
Source dataset
uspto-grants-2009_12
Patent number
US07638631B2

Reaction notes

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