HCID 11462285, compound → HCID 59655980, compound

HRID 2054597Notes

Reaction equation

C[Si](C)(C)CC[O:5][C:6](=[O:21])[CH2:7][CH2:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:10].Cl[C:25]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:28]=[C:27]([N:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][CH2:38]2)[N:26]=1>>[Cl:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:25]1[N:26]=[C:27]([N:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH2:40][CH2:39][CH2:38]3)[N:28]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:30]=1)[CH:12]=[C:11]2[C:9](=[O:10])[CH2:8][CH2:7][C:6]([OH:5])=[O:21]

Participants

Reactant 2

HCID 11462285HCID 11462285, compound

HCID 86595727HCID 86595727, compound

Product 1

HCID 59655980HCID 59655980, compound

Procedure

Arylation of 4-(5-chloro-1H-indol-3-yl)-4-oxo-butyric acid 2-trimethylsilanyl-ethyl ester with 1-(4-chloro-6-phenyl-[1,3,5]-triazin-2-yl)-1,2,3,4-tetrahydro-quinoline and subsequent hydrolysis as outlined previously yielded the titled compound. Rf 0.34 (5% methanol in dichloromethane); 1H NMR (THF-d8, 300 MHz) δ 9.21 (1H, s, ArH), 8.72 (1H, m, ArH), 8.59 (2H, d, J=7 Hz, ArH), 8.39 (1H, d, J=2 Hz, ArH), 7.95 (1H, d, J=8 Hz, ArH), 7.62-7.51 (3H, m, ArH), 7.35-7.15 (4H, m, ArH), 4.32 (2H, t, J=6 Hz, CH2), 3.30 (2H, t, J=7 Hz, CH2), 2.88 (2H, t, J=6 Hz, CH2), 2.72 (2H, t, J=7 Hz, CH2), 2.13 (2H, m, CH2); ESI-LCMS e/z calculated for C30H24ClN5O3 537.157, found 538 (M+H)+, 560 (M+Na)+.

Sources & evidence

ORD record: ord-71db438701764606af5c8ceff8abecef
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329680B2

Reaction notes

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