3-(Dimethylaminomethyl)-7-azaindole → HCID 21462982, compound

HRID 1940537Notes

Reaction equation

HRID 1940537 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.CN([CH2:20][C:21]1[C:29]2[C:24](=[N:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)C>CCO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:16][CH2:15][N:14]([CH2:20][C:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:13][CH:12]=1

Participants

4

Reactant 2

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 22729078HCID 22729078, compound

Product 1

HCID 21462982HCID 21462982, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Naphthalen-2-yl-1,2,3,6-tetrahydropyridine (597 mg, 2.9 mmol) was reacted with 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.9 mmol) as exemplified in Example 4 to give the title compound (619 mg, 63%) as tan crystals, m.p. 223°-225° C. (EtOH); (Found: C, 81.05; H, 6.24; N, 12.19. C23H21N3 requires C, 81.38; H, 6.24; N, 12.38%); δH (DMSO-d6) 2.60 (2H, m, tetrahydropyridinyl CH2), 2.72 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.16 (2H, d, J 2.7 Hz, tetrahydropyridinyl CH2), 3.78 (2H, s, ArCh2N), 6.34 (1H, m, CH=CR), 7.04 (1H, dd, J 7.5, 1.5 Hz, 5-H), 7.40 (1H, d, J 2.3 Hz, ArH), 7.44 (2H, m, ArH), 7.66 (1H, dd, J 1.6, 7.8 Hz, ArH), 7.86 (4H, m, ArH), 8.06 (1H, d, J 7.5 Hz, 4-H), 8.20 (1H, d, J 1.5 Hz, 6-H, and 11.48 (1H, br s, NH); m/z (CI+, NH3) 340 (M+1)+.

Sources & evidence

ORD record
ord-1d1baec4c0b04d0c947572b530e44da6
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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