Cesium carbonate → HCID 85470479, compound

HRID 1403733Notes

Reaction equation

C[C:2]1([CH3:27])[CH2:7][CH2:6][NH:5][S:4](=[O:9])(=[O:8])[N:3]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]2)=[CH:13][C:12]=1[F:26].[C:28]1(I)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:26][C:12]1[CH:13]=[C:14]([N:17]2[CH2:18][CH2:19][N:20]([C:23](=[O:25])[CH3:24])[CH2:21][CH2:22]2)[CH:15]=[CH:16][C:11]=1[CH2:10][N:3]1[CH:2]([CH3:27])[CH2:7][CH2:6][N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:4]1(=[O:9])=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 2-{[4-(4-acetylpiperazin-1-yl)-2-fluorophenyl]methyl}-3-methyl-1λ6,2,6-thiadiazinane-1,1-dione (200 mg, 0.52 mmol), PhI (212 mg, 1.04 mmol), Pd2(dba)3 (48 mg, 0.052 mmol), Xantphos (60 mg, 0.104 mmol), and Cs2CO3 (170 mg, 1.04 mmol) in 1,4-dioxane (3 mL) was heated at 100° C. in a microwave oven for 1 hour. The reaction mixture was concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford the title compound as light yellow oil (60 mg, 25%). 1H NMR (500 MHz, CDCl3) δ 7.54 (t, 1H), 7.35-7.41 (m, 4H), 7.27-7.29 (m, 1H), 6.69 (dd, 1H), 6.54 (dd, 1H), 4.49 (d, 1H), 4.28-4.35 (m, 2H), 3.90 (td, 1H), 3.76 (t, 2H), 3.61 (t, 2H), 3.53 (td, 1H), 3.14-3.20 (m, 4H), 2.14 (s, 3H), 1.98-2.02 (m, 1H), 1.75-1.78 (m, 1H), 1.25 (d, 3H); LCMS (ESI): m/z=461.7 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-a6bab4e8f6fc4b7897ace49b952bffd7
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912219B2

Reaction notes

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