HCID 89466854, compound → HCID 89466702, compound

HRID 240449Notes

Reaction equation

HRID 240449 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][N:18]2[CH2:21][C@H:22]([O:24][C:25]3[CH:30]=[N:29][C:28]([CH:31]4[CH2:33][CH2:32]4)=[CH:27][N:26]=3)[CH2:23][C@H:17]2[CH2:16]1)(=[O:14])=[O:13].[Cu][C:35]#[N:36]>CN(C)C=O>[CH:31]1([C:28]2[N:29]=[CH:30][C:25]([O:24][C@H:22]3[CH2:21][N:18]4[CH2:19][CH2:20][N:15]([S:12]([C:3]5[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=5[C:35]#[N:36])(=[O:14])=[O:13])[CH2:16][C@@H:17]4[CH2:23]3)=[N:26][CH:27]=2)[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 89466854HCID 89466854, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 89466702HCID 89466702, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of Example 201A (105 mg, 0.192 mmol) in N,N-dimethylformamide (1 mL) was added copper(I) cyanide (52 mg, 0.58 mmol), and the resulting mixture was heated at 120° C. and stirred for 24 hours. The cooled mixture was partitioned between water and ethyl acetate, and the organic layer was dried over Na2SO4. The drying agent was removed by filtration, the filtrate was concentrated in vacuo, and the residue was purified on silica gel using a solvent gradient of 0-60% ethyl acetate in hexanes. The title compound was obtained as a colorless solid (70 mg, 74%). 1H NMR (300 MHz, CDCl3) δ ppm 0.88-0.99 (m, 4H), 1.77-1.91 (m, 1H), 1.93-2.06 (m, 2H), 2.35 (dd, J=10.00, 5.26 Hz, 1H), 2.39-2.61 (m, 3H), 2.81-2.96 (m, 1H), 3.03 (dd, J=8.82, 2.37 Hz, 1H), 3.68 (dd, J=10.17, 6.78 Hz, 1H), 3.89 (dd, J=10.51, 1.70 Hz, 1H), 3.96-4.08 (m, 1H), 5.23-5.39 (m, 1H), 7.90-7.98 (m, 2H), 7.99-8.06 (m, 2H), 8.30 (s, 1H); MS (ESI) m/z 494 (M+H)+.

Workup

  1. customThe cooled mixture was partitioned between water and ethyl acetate
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified on silica gel using a solvent gradient of 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-42b628e04eb94588a1459f5e40bb9138
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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