Diisopropylethylamine → HCID 66833352, compound

HRID 2044089Notes

Reaction equation

Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[N:3]=1.OC(C(F)(F)F)=O.[C:29]1([C:35]2[CH2:39][C:38]3([CH2:44][CH2:43][CH2:42][NH:41][CH2:40]3)[O:37][N:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:4]2[N:3]=[C:2]([N:41]3[CH2:42][CH2:43][CH2:44][C:38]4([O:37][N:36]=[C:35]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:39]4)[CH2:40]3)[CH:10]=[CH:9][C:5]=2[C:6]([NH2:8])=[O:7])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-chloro-2-(4-(methylsulfonyl)phenylamino)nicotinamide (30 mg, 0.092 mmol), 3-phenyl-1-oxa-2,7-diazaspiro[4.5]dec-2-ene TFA salt (30.4 mg, 0.092 mmol) and N,N-diisopropylethylamine (0.064 mL, 0.368 mmol) in DMF (1 mL) was stirred at 120° C. for 20 h. The mixture was cooled to room temperature and purified by reverse phase HPLC, using Sunfire S10 30×250 mm column and eluting with 40% to 100% solvent B (10% MeOH-90% H2O-0.1% TFA) in solvent A (90% MeOH-10% H2O-0.1% TFA), to give a brown solid (12 mg, 21%). LCMS: (M+H)+=506.10. 1H NMR (400 MHz, acetonitrile-d3) δ ppm 7.69-7.80 (3H, m), 7.62-7.69 (2H, m), 7.55 (2H, d, J=9.03 Hz), 7.36-7.44 (3H, m), 6.28 (1H, d, J=9.04 Hz), 3.50-3.95 (4H, m), 3.08-3.38 (2H, m), 2.85 (3H, s), 2.01-2.13 (2H, m), 1.65-1.83 (2H, m).

Workup

temperatureThe mixture was cooled to room temperature
custompurified by reverse phase HPLC
washeluting with 40% to 100% solvent B (10% MeOH-90% H2O-0.1% TFA) in solvent A (90% MeOH-10% H2O-0.1% TFA)

Sources & evidence

ORD record: ord-cd96e694246e46f7b420ee020075dca7
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586751B2

Reaction notes

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