1-Propanol, 3-amino-2,2-dimethyl- → 4-[5-Bromo-6-(3-hydroxy-2,2-dimethyl-propylamino)-pyridine-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

HRID 723125Notes

Reaction equation

HRID 723125 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]([CH3:35])([CH3:34])[CH2:32][OH:33].C(Cl)Cl.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C1COCC1>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[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]([CH3:35])([CH3:34])[CH2:32][OH:33]

Participants

5

Reactant 3

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 21863450Trifluoroacetic acid methylene chlorideHCID 140043501tert-butyl N-[4-[(5-bromo-6-chloro-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 218866714-[5-Bromo-6-(3-hydroxy-2,2-dimethyl-propylamino)-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), 3-amino-2,2-dimethylpropanol (0.013 g, 0.133 mmol), THF [2 mL], followed by DCM/TFA (1:1) and reverse-phase HPLC to yield the title compound. ESI-MS (m/z): Calcd. for C17H22BrN3O3S3: 493.48 (M+H); found 493.1, 495.0.

Sources & evidence

ORD record
ord-1425dc185550456a9e32bdde092e0d05
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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