Sodium Carbonate → HCID 67437737、化合物

HRID 340153ノート

反応式

HRID 340153 の反応式
C([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:24]2[C:28]3[CH:29]=[CH:30][C:31](B4OC(C)(C)C(C)(C)O4)=[CH:32][C:27]=3[S:26][N:25]=2)[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH:9]=1.[N+:42]([C:45]1[CH:64]=[CH:63][C:48]([C:49]([O:51][C@H:52]2[C:56]3[N:57]=[CH:58][N:59]=[C:60](Cl)[C:55]=3[C@H:54]([CH3:62])[CH2:53]2)=[O:50])=[CH:47][CH:46]=1)([O-:44])=[O:43]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C=O)C>[N+:42]([C:45]1[CH:46]=[CH:47][C:48]([C:49]([O:51][C@H:52]2[C:56]3[N:57]=[CH:58][N:59]=[C:60]([C:31]4[CH:30]=[CH:29][C:28]5[C:24]([CH:14]([C:11]6[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=6)[CH2:15][NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:23])=[N:25][S:26][C:27]=5[CH:32]=4)[C:55]=3[C@H:54]([CH3:62])[CH2:53]2)=[O:50])=[CH:63][CH:64]=1)([O-:44])=[O:43]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 67438565Tert-butyl 2-(4-chlorophenyl)-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazol-3-yl)ethylcarbamateHCID 86651804(5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

生成物 1

HCID 67437737HCID 67437737、化合物収率 51.1%

試薬・触媒・溶媒 2

HCID 53485975CID 53485975触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

DMF (3 mL) and 2M aqueous Na2CO3 (0.38 mL, 0.76 mmol) were added to a nitrogen flushed flask containing tert-butyl 2-(4-chlorophenyl)-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazol-3-yl)ethylcarbamate (150 mg, 0.291 mmol), (5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (117 mg, 0.350 mmol) and dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (12 mg, 0.015 mmol). The mixture was heated at 80° C. for 1 hour. The mixture was cooled to room temperature and partitioned between EtOAc and water. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexanes:EtOAc (4:1 to 1:1) to give (5R,7R)-4-(3-(2-(tert-butoxycarbonylamino)-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (102 mg, 51%) as an oil. LCMS (APCI+) m/z 630, 632 [M+H]+; Rt=4.68 min.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with hexanes:EtOAc (4:1 to 1:1)

出典と根拠

ORDレコード
ord-c6cf6fa71c5d4bf6a9f46c5d7360bcb8
出典データセット
uspto-grants-2014_11
特許番号
US08895566B2

反応ノート

読み込み中…