2-Pyridinemethanamine → 4-[5-Bromo-6-[(pyridin-2-ylmethyl)-amino]-pyridine-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

HRID 2216076Notes

Reaction equation

HRID 2216076 reaction equation
C(OC(=O)[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])(C)(C)C.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C(Cl)(Cl)Cl.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>C1COCC1>[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42].[Br:24][C:22]1[CH:23]=[C:18]([S:15]([C:13]2[CH:14]=[C:10]([C:8]([NH2:7])=[NH:9])[S:11][C:12]=2[S:26][CH3:27])(=[O:17])=[O:16])[CH:19]=[N:20][C:21]=1[NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 19978452Chloroform trifluoroacetic acidHCID 140043501tert-butyl N-[4-[(5-bromo-6-chloro-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 218860994-[5-Bromo-6-[(pyridin-2-ylmethyl)-amino]-pyridine-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was conducted following the procedure for Example 164: step c, using {[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), (example 164: step b), 2-aminomethylpyridine (0.014 g, 0.133 mmol), THF [3 mL], followed by chloroform/TFA (1:1) to yield the title compound. ESI-MS (m/z): Calcd. for C17H16BrN5O2S3: 499.44 (M+H); found 499.1, 501.0.

Sources & evidence

ORD record
ord-a2c83d5aea974f1bbecdf84ca474b15f
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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