Diisopropylethylamine → HCID 11677409, compound

HRID 1992018Notes

Reaction equation

HRID 1992018 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[N:19]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][C:31]([C:34]#[N:35])=[CH:32][N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.CCN(C(C)C)C(C)C.[CH3:45][S:46]([CH2:49][CH2:50]OS(C)(=O)=O)(=[O:48])=[O:47]>C(Cl)Cl>[C:8]1([C:14]2[N:19]=[C:18]([CH:20]3[CH2:21][CH2:22][N:23]([CH2:50][CH2:49][S:46]([CH3:45])(=[O:48])=[O:47])[CH2:24][CH2:25]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][C:31]([C:34]#[N:35])=[CH:32][N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 184645972-(Methylsulfonyl)ethyl methanesulfonateHCID 86606280HCID 86606280, compound

Product 1

HCID 11677409HCID 11677409, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 5-cyano-1H-imidazole-2-carboxylic acid (6-cyclohex-1-enyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl-5-yl)-amide trifluoroacetic acid salt (57 mg, 0.11 mmol) in 5 mL of DCM was added DIEA (50.4 μL, 0.290 mmol) followed by 30.5 mg (0.150 mmol) of methanesulfonic acid 2-methanesulfonyl-ethyl ester (as prepared in Example 40, step(a)). The reaction was allowed to stir overnight, diluted with 20 mL of DCM, washed with satd aq NaHCO3 (1×20 mL) and dried over Na2SO4. Purification by preparative TLC (silica gel, 40% EtOAc-hexanes) afforded 22.3 mg (40%) of the title compound as a white solid. 1H-NMR (DMSO; 400 MHz): δ 10.02 (s, 1H), 8.24 (s, 1H), 8.11 (d, 1H, J=8.4 Hz), 7.18 (d, 1H, J=8.4 Hz), 5.96 (s, 1H), 3.04 (s, 3H), 3.02-2.99 (m, 3H), 2.73 (t, 2H, J=2.7 Hz), 2.39-2.37 (m, 2H), 2.11-2.05 (m, 4H), 1.85-1.64 (m, 10H). Mass Spectrum (ESI, m/z): Calcd. for C24H31N6O3S, 483.2 (M+H), found 483.3.

Workup

  1. washwashed with satd aq NaHCO3 (1×20 mL)
  2. dry with materialdried over Na2SO4
  3. customPurification by preparative TLC (silica gel, 40% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b010868968c74f7ea7a6ae0dc2e23910
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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