2-Methoxyethylamine → HCID 178495852, compound

HRID 2408522Notes

Reaction equation

HRID 2408522 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3(O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[NH:25][CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])=[CH:4][CH2:3]1.O=S(Cl)Cl.[CH3:36][O:37][CH2:38][CH2:39][NH2:40]>C(Cl)Cl.CCOC(C)=O>[CH3:31][C:2]1([CH3:1])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([NH:40][CH2:39][CH2:38][O:37][CH3:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[CH:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[NH:25][CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])=[CH:4][CH2:3]1

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 24386Thionyl ChlorideHCID 178424474HCID 178424474, compound

Product 1

HCID 178495852HCID 178495852, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(1-hydroxy-cyclohexyl)-phenyl]-amide (as prepared in Example 1, 42.0 mg, 0.100 mmol) in 1.5 mL of DCM at −15° C. was added SOCl2 (22.0 μL, 0.300 mmol) under Ar. After stirring at RT for 1 h, the mixture was cooled to −15° C. To the reaction was then added 2-methoxyethylamine (70.0 μL, 0.800 mmol) and the resulting mixture was stirred at RT for 2 h. The mixture was diluted with EtOAc (30 mL) and washed with H2O (2×10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (1-5% MeOH/DCM) to afford the title compound (21.7 mg, 46%) as a white solid. 1H-NMR (1:1 CDCl3/CD3OD; 400 MHz): δ 8.40 (d, 1H, J=8.6 Hz), 7.79 (s, 1H), 7.44 (m, 1H), 7.32 (br s, 1H), 5.81 (m, 1H), 3.48 (t, 2H, J=5.1 Hz), 3.27 (s, 3H), 2.60 (t, 2H, J=5.1 Hz), 2.35-2.45 (m, 2H), 2.28-2.35 (m, 2H), 2.09-2.15 (m, 2H), 1.87-1.98 (m, 2H), 1.68-1.78 (m, 2H), 1.61 (t, 2H, J=6.3 Hz), 1.34-1.60 (m, 4H), 1.12 (s, 6H). Mass spectrum (APCI-neg, m/z): Calcd. for C28H37N5O2, 474.3 (M−H), found 474.5.

Workup

  1. temperaturethe mixture was cooled to −15° C
  2. washwashed with H2O (2×10 mL) and brine (10 mL)
  3. dry with materialAfter drying over Na2SO4
  4. concentrationconcentrating in vacuo
  5. customthe residue was purified by silica gel chromatography (1-5% MeOH/DCM)

Sources & evidence

ORD record
ord-8929f362582d4e9c9e692c8add39708a
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

Loading…