Diglyme → HCID 66604824, compound

HRID 2410905Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[C:18]1([C:24]2[N:25]=[C:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])N=N[CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.COCCOCCOC>>[N:12]1([C:10]([C:7]2[CH:8]=[C:9]3[C:4]([C:3]4[CH:29]=[C:24]([C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:25]=[C:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:2]=4[NH:1]3)=[CH:5][CH:6]=2)=[O:11])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

Reactant 3

HCID 8150Diglyme

HCID 6917603HCID 6917603, compound

HCID 39710543(1H-Indol-6-yl)(morpholino)methanone

Product 1

HCID 66604824HCID 66604824, compound

Conditions

Temperature: 185 °C

Procedure

(1H-Indol-6-yl)(morpholino)methanone (200 mg, 0.869 mmol), ethyl 5-phenyl-1,2,4-triazine-3-carboxylate (299 mg, 1.303 mmol) and 1-methoxy-2-(2-methoxyethoxy)ethane (556 μL, 3.91 mmol) were mixed in a sealed microwave vial. The mixture was heated in microwave at 185° C. for 8 hrs. The mixture was purified using preparative HPLC to give titled product. MS (ESI) m/z 430.09 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.82 (s, 1H), 9.13 (s, 1H), 8.47 (d, 1H, J=7.9), 8.27 (d, 2H, J=7.7), 7.81 (s, 1H), 7.56(t, 2H, J=7.6), 7.44 (t, 1H, J=7.3), 7.36 (d, 1H, J=7.9), 4.57 (q, 2H, J=7.1), 3.67-3.45 (bm, 8H), 1.47 (t, 3H, J=7.1). NOE and ghmbc were used to confirm the structure.

Workup

customThe mixture was purified

Sources & evidence

ORD record: ord-8d61f24ad15e408bb1a2b7e5e5caa69d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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