Diisopropylethylamine → HCID 66649651, compound

HRID 420310Notes

Reaction equation

HRID 420310 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[CH2:8][NH:9][C@@H:10]1[C@@H:15]([OH:16])[C@H:14]([CH2:17][C:18]2[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[C:21]([N+:30]([O-:32])=[O:31])=[C:20]([F:33])[CH:19]=2)[CH2:13][S:12](=[O:35])(=[O:34])[CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[C:39](C1NC=CN=1)(C1NC=CN=1)=[O:40].CCN(C(C)C)C(C)C>C(#N)C.CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[CH2:8][N:9]1[C@@H:10]2[C@H:15]([C@H:14]([CH2:17][C:18]3[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:28])([F:29])[F:27])[C:21]([N+:30]([O-:32])=[O:31])=[C:20]([F:33])[CH:19]=3)[CH2:13][S:12](=[O:35])(=[O:34])[CH2:11]2)[O:16][C:39]1=[O:40])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 131729382HCID 131729382, compound

Product 1

HCID 66649651HCID 66649651, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R,4S,5S)-3-(3-tert-Butyl-benzylamino)-5-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol (1.39 g, 2.47 mmol) in ACN (4 mL) and DMF (2 mL) was added carbonyl-diimidazole (0.8 g 4.94 mmol), DIPEA (4.8 g, 3.71 mmol) and DMAP (30 mg, 0.247 mmol). The reaction mixture was refluxed for 2 days and then concentrated in vacuo. The title compound was obtained after flash-chromatography on silica gel (toluene-EtOAc 1:1): ESIMS [M+NH4]+=606; UPLC RtD=1.913 min; 1H NMR (600 MHz, DMSO-d6): δ 7.42 (s, 1H), 7.32 (d, 1H), 7.28 (t, 1H), 7.21 (s, 1H), 7.16 (d, 1H), 7.13 (d, 1H), 4.98 (q, 2H), 4.45 (d, 1H), 4.21 (m, 2H), 3.78 (m, 1H), 3.63 (m, 1H), 3.46 (t, 1H), 3.13 (m, 2H), 3.02 (m, 1H), 2.60 (m, 2H), 1.25 (s, 9H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce34a2615f8f4bd8b2e117af2158be8c
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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