Toluene → HCID 86678997, compound

HRID 2203362Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.C1(C)C=CC=CC=1.[NH2:30][C:31]1[C:32]2[C:57]([CH3:64])([C:58]([NH:60][NH:61][CH:62]=O)=O)[C:56](=[O:65])[NH:55][C:33]=2[N:34]=[C:35]([C:37]2[C:45]3[C:40](=[N:41][CH:42]=[CH:43][CH:44]=3)[N:39]([CH2:46][CH2:47][C:48]([F:54])([F:53])[C:49]([F:52])([F:51])[F:50])[N:38]=2)[N:36]=1>C1COCC1>[NH2:30][C:31]1[C:32]2[C:57]([CH3:64])([C:58]3[S:10][CH:62]=[N:61][N:60]=3)[C:56](=[O:65])[NH:55][C:33]=2[N:34]=[C:35]([C:37]2[C:45]3[C:40](=[N:41][CH:42]=[CH:43][CH:44]=3)[N:39]([CH2:46][CH2:47][C:48]([F:54])([F:53])[C:49]([F:52])([F:51])[F:50])[N:38]=2)[N:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Lawesson's reagent (133 mg, 0.328 mmol) was added to a toluene (5 mL) solution of the intermediate from Step B (170 mg, 0.298 mmol). THF (0.5 mL) was added to improve solubility and the reaction was heated to 100° C. for 1 hour in a screw cap vial. The reaction was then cooled and concentrated in vacuo. The crude product was purified by silica gel column chromatography using a hexanes/EtOAc gradient to give the title compound. Chiral separation using SFC on a Chiralcel OD column provided both enantiomers of the title compound. 1H NMR (600 MHz, CD3OD): δ 9.45 (s, 1H); 9.04 (dd, J=7.8, 1.2 Hz, 1H); 8.60 (dd, J=4.2, 1.2 Hz, 1H); 7.36 (dd, J=7.8, 4.2 Hz, 1H); 4.94 (t, J=8.4 Hz, 2H); 4.56 (bs, 2H), 3.01-2.92 (m, 2H); 1.98 (s, 3H). m/z=511.95 (M+H).

Workup

customcap vial
temperatureThe reaction was then cooled
concentrationconcentrated in vacuo
customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b99090405abb40cbae8d818bfb587502
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365574B2

Reaction notes

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