HCID 69021994, compound → HCID 22050800, compound

HRID 1867138Notes

Reaction equation

HRID 1867138 reaction equation
C(OC(=O)N[N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][N:18]3[C:23]([CH3:24])=[CH:22][C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=4[F:34])=[C:20]([Cl:35])[C:19]3=[O:36])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)(C)(C)C>CS(C)=O.O>[Cl:35][C:20]1[C:19](=[O:36])[N:18]([CH2:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][CH:9]=[CH:10]3)[C:23]([CH3:24])=[CH:22][C:21]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34]

Participants

4

Reactant 1

HCID 69021994HCID 69021994, compound

Product 1

HCID 22050800HCID 22050800, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

5-[3-Chloro-4-(2,4-difluorobenzyloxy)-6-methyl-2-oxo-2H-pyridin-1-ylmethyl]indole-1-carbamic acid tert-butyl ester (1.08 g, 2.1 mmol) dissolved in 40 mL of DMSO was stirred at 120° C. for 20 hours. The reaction was cooled to room temperature, diluted with water, and washed 5 times with ethyl acetate. The combined organics were washed 1 time with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. 1H NMR (300 MHz, DMSO-d6) δ 11.1 (br s, 1H), 7.67 (d, J=6.7 Hz, 1H), 7.36-7.32 (m, 2H), 7.23 (s, 1H), 7.18 (d, J=2.3 Hz, 1H), 6.93 (dd, J=8.4, 1.2 Hz, 1H), 6.57 (s, 1H), 6.38 (s, 1H), 5.37 (s, 2H), 5.29 (s, 2H), 2.35 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed 5 times with ethyl acetate
  3. washThe combined organics were washed 1 time with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29278f59ed30458ab7811c8a8be1b8f1
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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