HCID 18452815, compound → 3-(5-Methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-1-(1-ethylpropyl)-5-methyl-2(1H)-pyrazinone

HRID 2251006Notes

Reaction equation

HRID 2251006 reaction equation
[CH2:1]([CH:3]([N:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8](S(C)(=O)=O)[C:7]1=[O:17])[CH2:4][CH3:5])[CH3:2].Cl.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([CH3:30])[CH:29]=1)[NH:26][CH2:25][CH2:24]2>>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([CH3:30])[CH:29]=1)[N:26]([C:8]1[C:7](=[O:17])[N:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:11]=[C:10]([CH3:12])[N:9]=1)[CH2:25][CH2:24]2

Participants

3

Reactant 2

HCID 18452815HCID 18452815, compoundHCID 588451731-(1-Ethylpropyl)-5-methyl-3-(methylsulfonyl)-2(1H)-pyrazinone

Product 1

HCID 101321223-(5-Methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-1-(1-ethylpropyl)-5-methyl-2(1H)-pyrazinone

Procedure

Example 481 was prepared in a similar fashion as described for Example 413 using XXXIII and 5-methoxy-7-methylindoline hydrochloride as the starting materials. mp 138-140° C.; 1H NMR (300 MHz, CDCl3) δ 6.68 (d, J=2.2 Hz, 1 H), 6.56 (d, J=2.2 Hz, 1 H), 6.44 (s, 1 H), 4.90-4.79 (brs, 1 H), 4.34 (t, J=7.9 Hz, 2 H), 3.78 (s, 3 H), 3.05 (t, J=7.9 Hz, 2 H), 2.11 (s, 3 H), 2.00 (s, 3 H), 1.82-1.71 (m, 2 H), 1.67-1.60 (m, 2 H), 0.87 (t, J=7.4 Hz, 6 H); HRMS (ESI) calcd for C20H28N3O2 (M+H)+: 342.2182; found m/z 342.2196.

Workup

  1. customExample 481 was prepared in a similar fashion

Sources & evidence

ORD record
ord-0de55bb5876e48118d71c1b2296aeccb
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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