HCID 57794212, compound → HCID 57794356, compound

HRID 2099985Notes

Reaction equation

HRID 2099985 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([CH2:30][N:31]([CH2:33][CH2:34][O:35][CH3:36])[CH3:32])=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=4)[S:17][C:11]=3[N:10]([CH2:37][C:38]3[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=3[F:45])[C:9]2=[O:46])=[CH:4][CH:3]=1>N1C=CC=CC=1>[CH2:5]([NH:8][C:9]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([CH2:30][N:31]([CH2:33][CH2:34][O:35][CH3:36])[CH3:32])=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=4)[S:17][C:11]=3[N:10]([CH2:37][C:38]3[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=3[F:45])[C:9]2=[O:46])=[CH:6][CH:7]=1)=[O:46])[CH3:4]

Participants

3

Reactant 1

HCID 57794212HCID 57794212, compound

Product 1

HCID 57794356HCID 57794356, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl isothianate (36 mg) was added dropwise to a solution of the compound of Example 97 (0.10 g) in pyridine (1.00 ml) and the mixture was stirred at room temperature for 18 hours. After distilling off the solvent under reduced pressure, the obtained residue was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine and then dried over anhydride magnesium sulfate. The residue obtained by distilling off the solvent under the reduced pressure was recrystallized from methanol to give the title compound (0.06 g, 56%).

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. customthe obtained residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydride magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under the reduced pressure
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-4e6ff5bfb50d4d12b1f4bd4c0fd00f16
Source dataset
uspto-grants-2009_08
Patent number
US07569570B2

Reaction notes

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