Chloroform trifluoroacetic acid → N-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-4-sulfamoylbutyramide trifluoroacetate

HRID 723175Notes

Reaction equation

HRID 723175 reaction equation
C(Cl)(Cl)Cl.[F:5][C:6]([F:11])([F:10])[C:7]([OH:9])=[O:8].C(OC(=O)[NH:18][C:19](=[NH:53])[C:20]1[S:21][C:22]([S:51][CH3:52])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[NH:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][S:46](=[O:49])(=[O:48])[NH2:47])[CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:24]=1)(C)(C)C>>[F:5][C:6]([F:11])([F:10])[C:7]([OH:9])=[O:8].[C:19]([C:20]1[S:21][C:22]([S:51][CH3:52])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[NH:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][S:46](=[O:49])(=[O:48])[NH2:47])[CH:31]=[CH:32][CH:33]=2)(=[O:26])=[O:27])[CH:24]=1)(=[NH:18])[NH2:53]

Participants

3

Reactant 2

HCID 19978452Chloroform trifluoroacetic acidHCID 145857688tert-butyl N-[4-[3-[2-methyl-6-(4-sulfamoylbutanoylamino)phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 21886326N-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-4-sulfamoylbutyramide trifluoroacetateYield 36%

Procedure

A solution of dichloromethane/trifluoroacetic acid (1/1) [1 mL] was added (imino-{4-[6′-methyl-2′-(4-sulfamoyl-butyrylamino)-biphenyl-3-sulfonyl]-5-methylsulfanyl-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester (0.010 g, 0.015 mmol) [example 210, step a] at room temperature and stirred for 1 hour. The reaction mixture was evaporated and purified via reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to give the title compound (0.005 g, 36%) as a solid. 1H-NMR (MeOD): δ 8.30 (s, 1H), 8.04 (md, 1H, J=7.6 Hz), 7.88 (t, 1H, J=1.6 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.54 (md, 1H, J=7.6 Hz), 7.36 (t, 1H, J=7.6 Hz), 7.29 (d, 1H, J=6.8 Hz), 7.19 (d, 1H, J=8.0 Hz), 2.77–2.72 (m, 5H), 2.16 (t, 2H, J=7.2 Hz), 2.09 (s, 3H), 1.76 (m, 2H). ESI-MS (m/z): Calcd. for C23H26N4O5S4: 566.08; found: 567.1.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified via reverse-phase HPLC [acetonitrile/water (0.01% TFA)]

Sources & evidence

ORD record
ord-8cf8ed4380c042d79c5308ee7b44b6d2
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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