Benzoyl isothiocyanate → HCID 90111324, compound

HRID 521725Notes

Reaction equation

HRID 521725 reaction equation
[NH2:1][C:2]1([C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[CH2:6][N:5]([C:7]2[N:12]=[C:11]([O:13][CH3:14])[C:10]([F:15])=[C:9]([CH3:16])[N:8]=2)[CH2:4][CH:3]1[CH2:17][OH:18].[C:25]([N:33]=[C:34]=[S:35])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[F:15][C:10]1[C:11]([O:13][CH3:14])=[N:12][C:7]([N:5]2[CH2:4][CH:3]([CH2:17][OH:18])[C:2]([NH:1][C:34]([NH:33][C:25](=[O:32])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[S:35])([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[CH2:6]2)=[N:8][C:9]=1[CH3:16]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 90112662HCID 90112662, compound

Product 1

HCID 90111324HCID 90111324, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [4-amino-1-(5-fluoro-4-methoxy-6-methyl-pyrimidin-2-yl)-4-pyrazin-2-yl-pyrrolidin-3-yl]methanol (930 mg, 2.78 mmol) in tetrahydrofuran (29 mL) under a nitrogen atmosphere is added benzoyl isothiocyanate (613 μL, 4.45 mmol). After stirring the reaction at room temperature for 1 hour the solvent is removed under reduced pressure. The resulting residue is purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (1.32 g, 95%). ES/MS (m/e): 498 (M+1).

Workup

  1. customthe reaction at room temperature for 1 hour the solvent
  2. customis removed under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18ba413ccce54d0fbd197e6619a9560d
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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