Diisopropylethylamine → HCID 24875178, compound

HRID 1190189Notes

Reaction equation

HRID 1190189 reaction equation
[CH2:1]([N:3]([CH3:21])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[CH:8]=1)[CH3:2].CCN(C(C)C)C(C)C.[C:31]([C:33]1[O:37][C:36]([C:38](Cl)=[O:39])=[CH:35][CH:34]=1)#[N:32]>C(Cl)Cl>[CH2:1]([N:3]([CH3:21])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:38]([C:36]2[O:37][C:33]([C:31]#[N:32])=[CH:34][CH:35]=2)=[O:39])=[C:9]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 202590395-Cyano-2-furoyl chlorideHCID 58994576HCID 58994576, compound

Product 1

HCID 24875178HCID 24875178, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[3-(ethyl-methyl-amino)-propyl]-2-(4-methyl-piperidin-1-yl)-phenylamine (as prepared in the previous step, 32 mg, 0.11 mmol) in DCM (2 mL) at 0° C. was added DIEA (48 μL, 0.27 mmol) followed by 5-cyano-furan-2-carbonyl chloride (as prepared above, 22 mg, 0.16 mmol). The reaction was allowed to warm to RT overnight, at which time it was diluted with DCM (20 mL), washed with saturated aqueous NaHCO3 (10 mL), dried (Na2SO4) and concentrated in vacuo. Purification by preparative TLC (10% MeOH—CHCl3) afforded 20 mg (45%) of the title compound as an oily amber solid. 1H-NMR (CDCl3; 400 MHz): δ 9.69 (s, 1H), 8.38 (d, 1H, J=8.4 Hz), 7.26 (d, 1H, J=3.6 Hz), 7.05 (d, 1H, J=2.0 Hz), 7.00-6.97 (m, 1H), 6.91 (d, 1H, J=4.0 Hz), 3.01-2.98 (m, 2H), 2.78-2.64 (m, 7H), 2.50 (s, 3H), 2.04-1.98 (m, 2H), 1.89-1.85 (m, 2H), 1.63-1.46 (m, 5H), 1.25 (t, 3H, J=4.6 Hz), 1.10 (d, 3H, J=6.4 Hz), 0.93-0.89 (m, 2H). Mass spectrum (ESI, m/z) calcd for C24H32N4O2, 409.2 (M+H). found 409.3.

Workup

  1. washwashed with saturated aqueous NaHCO3 (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative TLC (10% MeOH—CHCl3)

Sources & evidence

ORD record
ord-fb438b330a944119a5203daa48ae376c
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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