Pyridine → tert-butyl-N-[5-(benzenesulfonamido)-6-(2-phenylethynyl)pyridin-2-yl]-carbamate

HRID 535392Notes

Reaction equation

HRID 535392 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:15][C:16](=[O:33])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([C:25]#[C:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:19]=1)([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>C(Cl)Cl>[C:11]([O:15][C:16](=[O:33])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[C:20]([C:25]#[C:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:19]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 86694370tert-butyl-N-[5-amino-6-(2-phenylethynyl)pyridin-2-yl]carbamate

Product 1

HCID 86694377tert-butyl-N-[5-(benzenesulfonamido)-6-(2-phenylethynyl)pyridin-2-yl]-carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulfonyl chloride (20 μl, 0.4 mmol) diluted with 400 μl DCM is added to a mixture of tert-butyl-N-[5-amino-6-(2-phenylethynyl)pyridin-2-yl]carbamate B5a (40 mg, 0.13 mmol), pyridine (32 μl, 0.4 mmol) and 400 μl DCM at RT and stirred for 1 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 37 mg (64%). HPLC-MS: M+H=450; tR=2.16 min (*Method—2).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-99758052800f475086917d83560cddc2
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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