Triethylamine → HCID 19040757, compound

HRID 1683910Notes

Reaction equation

HRID 1683910 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].[C:16]([C:21]1[N:26]=[N:25][C:24]([S:27][CH3:28])=[N:23][C:22]=1Cl)([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C>O1CCCC1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:22]3[N:23]=[C:24]([S:27][CH3:28])[N:25]=[N:26][C:21]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-CarboxylateHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 19040757HCID 19040757, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 6-carbethoxy-5-chloro-3-methylthio-1,2,4-triazine [Pesson, M. et al., Eur. J. Med. Chem., 269 (1972)] were used. Triethylamine was used as base, tetrahydrofuran was used as solvent, and the reaction was stirred at room temperature for 1 hour. Chromatography afforded the title compound (53%) as an orange solid: mp, 197.0°-199.0° C. with effervescence; 13C NMR (DMSO-d6) δ173.2, 165.5, 150.5, 133.9, 132.5, 127.7, 127.1, 123.9, 116.8, 113.0, 112.2, 111.5, 62.0, 60.0, 45.2, 23.1, 14.0, 13.2; LRMS (m/z, relative intensity) 400 (M30 , 11 ), 386 (5), 195 (11), 163(13), 58 (100). Anal. calcd. for C19H24N6O2S.0.3 H2O: C, 56.22 ; H, 6.11; N, 20.70. Found: C, 55.50; H, 5.89; N, 20.33.

Sources & evidence

ORD record
ord-ff21f4d3356b4bd0b4ba0c2dcc88eaf2
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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