Diisopropylethylamine → HCID 66970182, compound

HRID 1360343Notes

Reaction equation

HRID 1360343 reaction equation
[CH2:1]([C:3]1[C:12]2[C:11](=[O:13])[O:10][C:9]([C:14]3[C:15](F)=[N:16][CH:17]=[CH:18][CH:19]=3)=[N:8][C:7]=2[CH:6]=[C:5]([O:21][CH3:22])[CH:4]=1)[CH3:2].[NH:23]1[CH2:27][CH2:26][C@@H:25]([N:28]2[CH2:33][CH2:32][S:31](=[O:35])(=[O:34])[CH2:30][CH2:29]2)[CH2:24]1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH2:1]([C:3]1[C:12]2[C:11](=[O:13])[O:10][C:9]([C:14]3[C:15]([N:23]4[CH2:27][CH2:26][CH:25]([N:28]5[CH2:29][CH2:30][S:31](=[O:35])(=[O:34])[CH2:32][CH2:33]5)[CH2:24]4)=[N:16][CH:17]=[CH:18][CH:19]=3)=[N:8][C:7]=2[CH:6]=[C:5]([O:21][CH3:22])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57340965HCID 57340965, compoundHCID 59755951HCID 59755951, compound

Product 1

HCID 66970182HCID 66970182, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 5-ethyl-2-(2-fluoropyridin-3-yl)-7-methoxy-4H-benz[d][1,3]oxazin-4-one (50.0 mg, 0.17 mmol) in anhydrous 1,4-dioxane (850 μL) was added compound Z (52.9 mg, 0.22 mmol) and diisopropylethyl amine (120 μL, 0.85 mmol) at room temperature under N2 overnight. The solution was concentrated, and the resulting residue was purified on a Biotage 40M amine column using a gradient of 20-75% ethyl acetate/hexanes to obtain the title compound. The fractions containing the title compound were combined and concentrated by speedvac to afford the title compound as a yellow oil (19.2 mg, 23% yield). 1H NMR (CDCl3, 400 MHz) δ: 8.33 (dd, 1H, J=1.0 Hz), 8.1 (d, 1H, J=7.0 Hz), 6.92 (dd, 2H, J=2.5 Hz), 6.83 (m, 1H), 3.93 (s, 3H), 3.83 (m, 1H), 3.62 (m, 2H), 3.39 (m, 1H), 3.26 (m, 1H), 3.22 (m, 4H), 3.17 (m, 6H), 2.16 (m, 1H), 1.94 (m, 1H), 1.29 (t, 3H, J=7.5 Hz); ESMS m/z 485.2 [M+H]+.

Workup

  1. concentrationThe solution was concentrated
  2. customthe resulting residue was purified on a Biotage 40M amine column

Sources & evidence

ORD record
ord-39fab3688bb941fe84e4c5095b488b15
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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