Lawesson's reagent → HCID 71100907, compound

HRID 80692Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:47])[NH:10][C:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][N:13]1[C:20](=[O:46])[C:21]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:22]([C:24](=O)[NH:25][CH2:26][C:27](=O)[CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:23]=[C:12]21)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:57])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:47])[NH:10][C:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][N:13]1[C:20](=[O:46])[C:21]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:22]([C:24]3[S:57][C:27]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[CH:26][N:25]=3)[N:23]=[C:12]21)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of benzyl(3-(benzyloxy)-2-((3-(4-fluorophenyl)-2-oxopropyl)carbamoyl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate, Intermediate 7 (120 mg, 0.188 mmol) in toluene was added Lawesson's Reagent (76 mg, 0.188 mmol) and stirred for 15 min at room temperature, 30 min at 60° C. and 2 h at 100° C. The resulting clear yellow mixture was then cooled, concentrated and purified by preparative HPLC to provide the title compound (60 mg, 0.094 mmol, 50.2% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (1H, s), 7.47-7.52 (2H, m), 7.29-7.39 (8H, m), 7.17 (2H, dd, J=8.28, 5.27 Hz), 6.94-7.07 (3H, m), 5.38 (2H, s), 5.09 (2H, s), 4.09-4.19 (4H, m), 2.69-2.84 (2H, m), 2.49 (1H, br. s.), 1.94-2.04 (4H, m), 1.65-1.76 (2H, m). LCMS (M+H)=637.27.

Workup

temperatureThe resulting clear yellow mixture was then cooled
concentrationconcentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-5a73471ae8b74fd9a9ebfe380a750ebe
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846659B2

Reaction notes

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