N-Methyl-1-(1-methyl-1H-indol-6-yl)methanamine → HCID 66967114, compound

HRID 1362377Notes

Reaction equation

HRID 1362377 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH3:13])=[CH:6][CH:5]=1.Cl.[O:15]=[C:16]1[NH:25][C:24]2[N:23]=[CH:22][C:21](/[CH:26]=[CH:27]/[C:28](O)=[O:29])=[CH:20][C:19]=2[CH2:18][CH2:17]1>>[CH3:1][N:2]([CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH3:13])=[CH:6][CH:5]=1)[C:28](=[O:29])[CH:27]=[CH:26][C:21]1[CH:22]=[N:23][C:24]2[NH:25][C:16](=[O:15])[CH2:17][CH2:18][C:19]=2[CH:20]=1

Participants

3

Reactant 2

HCID 18525770N-Methyl-1-(1-methyl-1H-indol-6-yl)methanamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

Product 1

HCID 66967114HCID 66967114, compoundYield 65%

Procedure

According to the procedure of Example 35g methyl-(1-methyl-1H-indol-6-ylmethyl)-amine (129 mg, 0.74 mmol) and (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3yl)acrylic acid hydrochloride (190 mg, 0.75 mmol), were coupled to give crude product. Purification by column chromatography (silica gel, 5% MeOH/CH2Cl2) gave the title compound (180 mg, 65%) as a pink solid and a mixture of amide rotomers: 1H NMR (400 MHz, DMSO-d6) δ 10.64-10.62 (m, 1H), 8.36-8.33 (m, 1H), 8.07-8.06 (m, 1H), 7.55-7.47 (m, 2H), 7.39-7.21 (m, 3H), 6.95-6.88 (m, 1H), 6.38-6.37 (m, 1H), 4.89-4.71 (m, 2H), 3.76-3.74 (m, 3H), 3.08-2.85 (m, 5H), 2.54-2.52 (m, 2H); ESI MS m/z 375 [C22H22N4O2+H]+.

Workup

  1. customto give crude product
  2. customPurification by column chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-77d0c3bc8b7b44919bbb5f6f054b3d00
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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