1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 11383345, compound

HRID 751374Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][NH:27][CH3:28]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[N:27]([CH2:26][CH2:25][N:24]([CH3:29])[CH3:23])[CH3:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

HCID 860359201-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde

Product 1

HCID 11383345HCID 11383345, compoundYield 42%

Procedure

1-(4-tert-Butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde is reacted with N,N,N′-trimethylethylenediamine as described in Step 2 of Example 29 to afford 1-(4-tert-butylphenyl)-2-[(2-dimethylaminoethyl)-methylamino]-1H-indole-3-carboxaldehyde (42% yield) as a light tan solid. TLC (silica gel, 7N NH3 in methanol/MeOH/Ethyl acetate (0.1:2:10 mL)) Rf 0.29. ESI/MS 378 (M+H); RT 3.43 min. NMR10.18 (1H, s); 8.10 (1H, d, J=9 Hz); 7.66 (2H, d); 7.48 (2H, d); 7.17 (1H, t); 7.08 (1H, t); 6.88 (1H, d, J=9 Hz); 3.21 (2H, t); 3.02 (3H, s); 2.18 (2H, t); 2.00 (6H, t); 1.36 (9H, s).

Sources & evidence

ORD record: ord-99dd5509691c40b3b3095799f9a8a240
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405300B2

Reaction notes

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