Sodium Carbonate → HCID 67437737, compound

HRID 340153Notes

Reaction equation

HRID 340153 reaction equation
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]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 67438565HCID 67438565, compoundHCID 86651804(5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

Product 1

HCID 67437737HCID 67437737, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c6cf6fa71c5d4bf6a9f46c5d7360bcb8
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

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