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

HRID 723200Notes

Reaction equation

HRID 723200 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-c20fade4af3041479f8b0c48cf0b6670
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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