Trifluoroacetic acid → HCID 21886145, compound

HRID 723153Notes

Reaction equation

HRID 723153 reaction equation
C(OC(=O)NC(C1SC(SC)=C(S(C2C=C(Br)C3N(CC4C=CC([N+]([O-])=O)=CC=4F)C=NC=3C=2)(=O)=O)C=1)=N)(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]=[CH:71][C:70]([N+:73]([O-:75])=[O:74])=[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]=[CH:71][C:70]([N+:73]([O-:75])=[O:74])=[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

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 145857607HCID 145857607, compoundHCID 145857670HCID 145857670, compound

Product 1

HCID 21886145HCID 21886145, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ({4-[7-bromo-1-(2-fluoro-4-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-4-nitro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophen-2-yl)-imino-methyl)-carbamic acid tert-butyl ester ((from above step a) 0.005 g, 0.007 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 h. Solvents were removed in vacuo. Preparatory HPLC (10–80% acetonitrile in 1% TFA/water over 30 min.) afforded the product 4-[7-bromo-3-(2-fluoro-4-nitro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate (0.002 g, 47%) as a white solid. 1H NMR (MeOD): δ 8.714 (s, 1H), 8.308 (s, 1H), 8.231 (d, 1H, J=1.6 Hz), 8.106 (m, 2H), 8.047 (d, 1H, J=0.8 Hz), 7.556 (t, 1H, J=8.4 Hz), 5.854 (s, 2H), 2.630 (s, 3H). C20H15BrFN5O4S3: 583.95 (M+1) found 585.05.

Workup

  1. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-eb8d163e53eb4f809dbd768beacbbb51
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…