4-Pyridinemethanamine → tert-butyl N-[4-[[5-bromo-6-(pyridin-4-ylmethylamino)-3-pyridinyl]sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723122Notes

Reaction equation

HRID 723122 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:10]1[S:11][C:12]([S:26][CH3:27])=[C:13]([S:15]([C:18]2[CH:19]=[N:20][C:21](Cl)=[C:22]([Br:24])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C1COCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:10]1[S:11][C:12]([S:26][CH3:27])=[C:13]([S:15]([C:18]2[CH:19]=[N:20][C:21]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[C:22]([Br:24])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 140043501tert-butyl N-[4-[(5-bromo-6-chloro-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857702tert-butyl N-[4-[[5-bromo-6-(pyridin-4-ylmethylamino)-3-pyridinyl]sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a vessel containing a stir bar was added {[4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.035 g, 0.066 mmol), 4-aminomethylpyridine (0.015 g, 0.133 mmol), THF [3 mL]. The reaction vessel was sealed and heated to 70° C. for 18 hours, cooled to room temperature and concentrated in vacuo. The crude residue was dissolved in a solution of chloroform/trifluoroacetic acid (1/1) [2 mL] and was allowed to stir at room temperature for 2 hours. The reaction was concentrated in vacuo followed by reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to give the title compound. ESI-MS (m/z): Calcd. for C17H16BrN5O2S3: 499.44 (M+H); found 498.0, 500.0.

Workup

  1. additionTo a vessel containing a stir bar
  2. customThe reaction vessel was sealed
  3. temperaturecooled to room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved in a solution of chloroform/trifluoroacetic acid (1/1) [2 mL]
  6. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-89a9e05d69b646d09d583f81ed3ac3a4
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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