Trifluoroacetic acid → HCID 21886042, compound

HRID 723152Notes

Reaction equation

HRID 723152 reaction equation
C(OC(=O)[NH:7][C:8]([C:10]1[S:11][C:12]([S:39][CH3:40])=[C:13]([S:15]([C:18]2[CH:37]=[C:36]([Br:38])[C:21]3[N:22]([CH2:25][C:26]4[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=4[F:35])[CH:23]=[N:24][C:20]=3[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])(C)(C)C.C(OC(=O)[NH:48][C:49]([C:51]1[S:52][C:53]([S:80][CH3:81])=[C:54]([S:56]([C:59]2[CH:78]=[C:77]([Br:79])[C:62]3[N:63]=[CH:64][N:65]([CH2:66][C:67]4[CH:72]=[C:71]([N+:73]([O-:75])=[O:74])[CH:70]=[CH:69][C:68]=4[F:76])[C:61]=3[CH:60]=2)(=[O:58])=[O:57])[CH:55]=1)=[NH:50])(C)(C)C.[F:83][C:84]([F:89])([F:88])[C:85]([OH:87])=[O:86]>C(Cl)Cl>[F:83][C:84]([F:89])([F:88])[C:85]([OH:87])=[O:86].[Br:79][C:77]1[C:62]2[N:63]=[CH:64][N:65]([CH2:66][C:67]3[CH:72]=[C:71]([N+:73]([O-:75])=[O:74])[CH:70]=[CH:69][C:68]=3[F:76])[C:61]=2[CH:60]=[C:59]([S:56]([C:54]2[CH:55]=[C:51]([C:49]([NH2:50])=[NH:48])[S:52][C:53]=2[S:80][CH3:81])(=[O:57])=[O:58])[CH:78]=1.[F:83][C:84]([F:89])([F:88])[C:85]([OH:87])=[O:86].[Br:38][C:36]1[C:21]2[N:22]([CH2:25][C:26]3[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=3[F:35])[CH:23]=[N:24][C:20]=2[CH:19]=[C:18]([S:15]([C:13]2[CH:14]=[C:10]([C:8]([NH2:9])=[NH:7])[S:11][C:12]=2[S:39][CH3:40])(=[O:17])=[O:16])[CH:37]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 140043488HCID 140043488, compoundHCID 145857700HCID 145857700, compound

Product 2

HCID 21886042HCID 21886042, compoundYield 47%HCID 21886263HCID 21886263, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ({4-[7-bromo-1-(2-fluoro-5-nitro-benzyl)-1H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophen-2-yl}-imino-methyl)-carbamic acid tert-butyl ester and ({4-[7-bromo-3-(2-fluoro-5-nitro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophen-2-yl}-imino-methyl)-carbamic acid tert-butyl ester ((from above step d) 0.015 g, 0.022 mmol) in CH2Cl2 (1 mL) was cooled to 0° C. and treated with 25% trifluoroacetic acid in CH2Cl2 (1.00 mL). The mixture was allowed to warm to room temperature and was stirred 3.2 h. The solvents were removed in vacuo. Preparatory HPLC (10–80% acetonitrile in 1% TFA/water over 30 min.) afforded the products 4-[7-bromo-3-(2-fluoro-5-nitro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate (0.002 g, 47%) and 4-[7-bromo-1-(2-fluoro-5-nitro-benzyl)-1H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate (0.002 g, 47%) as white solids.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ce3ee9ade7a947b4b8b5fb086f44a903
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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