Phenyl isocyanate → HCID 67323590, compound

HRID 1846641Notes

Reaction equation

HRID 1846641 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:14]([NH:15][C:16](=[O:24])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)=[CH:13][C:12]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:11][N:10]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[Na+].[Na+].[C:35]1([N:41]=[C:42]=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[Cl:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:16]([NH:15][C:14]1[C:9]([N:6]2[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:42]([NH:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:43])[CH2:8][CH2:7]2)=[N:10][CH:11]=[C:12]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:13]=1)=[O:24]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 10340Sodium CarbonateHCID 67342451HCID 67342451, compound

Product 1

HCID 67323590HCID 67323590, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.028 g (0.066 mmol) of N-(4-aminomethyl-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl)-3-chloro-benzamide in a mixture of acetonitrile (0.5 mL) and saturated aqueous sodium carbonate (0.5 mL) is added 0.0086 mL (0.11 mmol) of phenylisocyanate. The mixture is stirred at room temperature for 6 hours then concentrated under reduced pressure. The residue is diluted with water causing a gummy solid to form. The aqueous phase is decanted off and the solid is rinsed and decanted with water and then dried. The residue is purified by preparative thin layer chromatography to give 0.016 mg (44%) of the title compound (110) as a clear resin. [M+H]+=542.7.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionThe residue is diluted with water causing a gummy solid
  3. customto form
  4. customThe aqueous phase is decanted off
  5. washthe solid is rinsed
  6. customdecanted with water
  7. customdried
  8. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-85150b4251b3449db12b3fd2c9e050d8
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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