Ethyl Acetate → tert-butyl N-[4-[3-[2-[(2-bromoacetyl)amino]-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216155Notes

Reaction equation

HRID 2216155 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([C:10]1[S:11][C:12]([S:32][CH3:33])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[NH2:31])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[Br:35][CH2:36][C:37](Br)=[O:38].CCN(C(C)C)C(C)C.CCOC(C)=O>C(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([C:10]1[S:11][C:12]([S:32][CH3:33])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:25]([NH:31][C:37](=[O:38])[CH2:36][Br:35])=[CH:26][CH:27]=[CH:28][C:29]=3[CH3:30])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857705tert-butyl N-[4-[3-[2-[(2-bromoacetyl)amino]-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 76.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Following the procedure described for Example 234, step a, reaction of {[4-(6′-amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (137 mg, 0.265 mmol, as prepared in Example 25, step c), bromoacetyl bromide (28 μL, 0.32 mmol), and DIEA (70 μL, 0.40 mmol) in chloroform (3 mL) afforded 129 mg (76%) of the title compound as a yellow foamy solid after chromatography (PTLC, 10% EtOAc in DCM, 2×1500μ SiO2 plate). 1H-NMR (CDCl3; 400 MHz): δ 8.05–8.10 (m, 1H), 7.85–7.95 (m, 2H), 7.65–7.73 (m, 2H), 7.46–7.51 (m, 1H), 7.35 (t, 1H, J=7.9 Hz), 7.16 (d, 1H, J=7.7 Hz), 3.64 and 3.74 (AB quartet, 2H, J=14.0 Hz), 2.60 (s, 3H), 2.03 (s, 3H), 1.52 (s, 9H). ESI-MS (m/z): Calcd. for C26H28BrN3O5S3: 637.0 (M+H); found: 637.8, 639.8, 538.0, 540.0 (M−Boc).

Sources & evidence

ORD record
ord-500b5dc0bb83482ab477a825383a3ca5
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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