Water → HCID 118274327, compound

HRID 522215Notes

Reaction equation

HRID 522215 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]([CH3:15])[CH2:13][C:12]3[C:8]4[C:9](=[N:16][CH:17]=[CH:18][C:7]=4[C:6]=2[CH:19]=1)[NH:10][CH:11]=3.[H-].[Na+].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]([CH3:15])[CH2:13][C:12]3[C:8]4[C:9](=[N:16][CH:17]=[CH:18][C:7]=4[C:6]=2[CH:19]=1)[N:10]([S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29])[CH:11]=3

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 118274291HCID 118274291, compound

Product 1

HCID 118274327HCID 118274327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 41B (18.49 g, 73.0 mmol) in N,N-dimethylformamide (146 mL) at room temperature under nitrogen was added sodium hydride (4.38 g, 110 mmol) in portions. The mixture was stirred for 30 minutes and p-toluenesulfonyl chloride (15.31 g, 80 mmol) was added in portions over 10 minutes. The mixture was stirred overnight at room temperature, poured into water and filtered. The solid was washed with heptanes and placed in a vacuum oven overnight at 50° C. The residue was taken up in dichloromethane/methanol and concentrated to give a solid containing ˜10% unreacted starting material. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (d, J=5.3 Hz, 1H), 8.01 (d, J=8.4 Hz, 2H), 7.76 (d, J=10.4 Hz, 1H), 7.71 (s, 1H), 7.61 (d, J=5.5 Hz, 1H), 7.41 (d, J=8.1 Hz, 2H), 7.31-7.25 (m, 2H), 4.10 (s, 2H), 2.89 (s, 3H), 2.33 (s, 3H). MS (ESI+) m/z 408.5 (M+H)+.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. filtrationfiltered
  3. washThe solid was washed with heptanes
  4. customplaced in a vacuum oven overnight at 50° C
  5. concentrationconcentrated
  6. customto give a solid
  7. additioncontaining ˜10%

Sources & evidence

ORD record
ord-c905712709cd400187b027c4a9b9d2c6
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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