HCID 11462285, compound → HCID 69298124, compound

HRID 2054596Notes

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]([O:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]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:30]=[C:29]([O:31][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[N:28]=[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:26]=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 86595726HCID 86595726, compound

Product 1

HCID 69298124HCID 69298124, compound

Procedure

Arylation of 4-(5-chloro-1H-indol-3-yl)-4-oxo-butyric acid 2-trimethylsilanyl-ethyl ester with 1-(4-chloro-6-cyclopentyloxy-[1,3,5]-triazin-2-yl)-1,2,3,4-tetrahydro-quinoline and subsequent hydrolysis as outlined previously yielded the titled compound. Rf 0.30 (5% methanol in dichloromethane); 1H NMR (DMSO-d6, 300 MHz) δ 8.97 (1H, s, ArH), 8.55 (1H, d, J=9 Hz, ArH), 8.18 (1H, d, J=2 Hz, ArH), 7.81 (1H, d, J=8 Hz, ArH), 7.35-7.10 (4H, m, ArH), 5.44 (1H, m, CH), 4.08 (2H, t, J=6 Hz, CH2), 3.22 (2H, t, J=6 Hz, CH2), 2.78 (2H, t, J=6 Hz, CH2), 2.58 (2H, t, J=6 Hz, CH2), 2.01-1.61 (10H, m, CH2); ESI-LCMS e/z calculated for C29H28ClN5O4 545.183, found 546 (M+H)+, 568 (M+Na)+.

Sources & evidence

ORD record: ord-63cf90bb6d424e009e2ac56deb4053fc
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329680B2

Reaction notes

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