6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → HCID 18545946, compound

HRID 1267160Notes

Reaction equation

HRID 1267160 reaction equation
[CH:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([CH2:12][CH2:13]S(C)(=O)=O)[CH2:4]1)=[O:2].[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([C:28]3[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=3)=[CH:24][NH:25]2)=[CH:21][CH:20]=1>CC(C)=O>[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([C:28]3[CH2:29][CH2:30][N:31]([CH2:13][CH2:12][CH:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[N:3]([CH:1]=[O:2])[CH2:4]4)[CH2:32][CH:33]=3)=[CH:24][NH:25]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 18545866HCID 18545866, compound

Product 1

HCID 18545946HCID 18545946, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

From 19b and 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole. Mp 183-5° C. (from acetone). 1H NMR (DMSO-d6, the spectrum shows hindered rotation which is eliminated by heating above 100° C.) δ 1.60-1.80 (m, 1H), 1.95-2.10 (m, 1H), 2.35-2.55 (m, 4H), 2.70 (t, 2H), 3.15 (s, 2H), 3.35-3.55 (m, 1H), 3.65 (dd, 0.76H), 3.90 (dd, 0.24H), 4.10 (t, 0.76H), 4.30 (t, 0.24H), 6.15 (s, 1H), 6.95-7.15 (m, 2H), 7.25 (t, 1H), 7.35 (d, 1H), 7.40-7.50 (m, 3H), 7.80 (d, 0.76H), 7.90 (d, 0.24H), 8.50 (s, 0.24H), 9.05 (s, 0.76H), 11.20 (s, 1H). MS m/z (%): 406 (MH+, 100%), 377 (5%), 244 (15%).

Sources & evidence

ORD record
ord-652c02dd76944ccfa4684cdbb59f413b
Source dataset
uspto-grants-2003_04
Patent number
US06552044B2

Reaction notes

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