Diisopropylethylamine → HCID 59225732, compound

HRID 387495Notes

Reaction equation

C(O[C:9]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:24]2[N:28]([CH3:29])[N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])C1C=CC=CC=1.CCN([CH:40]([CH3:42])[CH3:41])C(C)C>CN(C1C=CN=CC=1)C.ClCCl>[O:19]1[C:17]2[CH:16]=[CH:12][CH:42]=[CH:40][C:41]=2[CH:21]=[C:20]1[C:9]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:24]2[N:28]([CH3:29])[N:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10]

Participants

Conditions

Temperature: 30 °C

Procedure

Under an atmosphere of argon, acid chloride 12 (10.8 mg, 60 μmol) was added in portions to a stirred solution of 11 (24 mg, 50 μmol), Hünig's base (26 μL, 19 mg, 15 μmol), and DMAP (0.6 mg, 5.0 μmol) in dichloromethane (250 μL) at room temperature. The reaction was stirred for 10 minutes then heated to 30° C. for 20 minutes. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 13 (21.3 mg, 87%) as a solid: LRESIMS m/z 492 [M+H]+, calcd. for C23H20F3N3O4S1 492.1.

Workup

concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-364e4e33ce154748bea97b47383e89b8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372991B2

Reaction notes

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