Trifluoroacetic acid → HCID 69299387, compound

HRID 2054595Notes

Reaction equation

HRID 2054595 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:42])[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)[N:13]([C:21]2[N:26]=[C:25]([N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28]3)[N:24]=[C:23]([N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[N:22]=2)[CH:12]=1)=[O:10].FC(F)(F)C(O)=O>ClCCl>[Cl:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:21]1[N:26]=[C:25]([N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28]3)[N:24]=[C:23]([N:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[N:22]=1)[CH:12]=[C:11]2[C:9](=[O:10])[CH2:8][CH2:7][C:6]([OH:42])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69298187HCID 69298187, compound

Product 1

HCID 69299387HCID 69299387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-{5-chloro-1-[4-(2,3-dihydro-indol-1-yl)-6-piperidin-1-yl-[1,3,5]-triazin-2-yl]-1H-indol-3-yl}-4-oxo-butyric acid 2-trimethylsilanyl-ethyl ester (0.198 g, 0.314 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (0.25 mL, 3.25 mmol). Upon completion (TLC 5% methanol in dichloromethane), the solution was concentrated in vacuo to yield the titled compound as a white solid. Rf 0.21 (5% methanol in dichloromethane); 1H NMR (THF-d8, 300 MHz) δ 9.04 (1H, s, ArH), 8.73 (1H, d, J=9 Hz, ArH), 8.39 (1H, d, J=2 Hz, ArH), 8.34 (1H, d, J=7 Hz, ArH), 7.32 (1H, dd, J=9, 2 Hz, ArH), 7.23-7.16 (2H, m, ArH), 6.95 (1H, t, J=7 Hz, ArH), 4.40 (2H, m, CH2), 3.97 (4H, m, CH2), 3.28-3.18 (4H, m, CH2, CH2), 2.71 (2H, t, J=6 Hz, CH2), 1.75-1.65 (6H, m, NCH2); ESI-LCMS e/z calculated for C28H27ClN6O3 530.183, found 531 (M+H)+, 553 (M+Na)+.

Workup

  1. concentrationUpon completion (TLC 5% methanol in dichloromethane), the solution was concentrated in vacuo

Sources & evidence

ORD record
ord-01169dfb7bf24e018ff4312fad3e0dea
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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