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

HRID 2216158Notes

Reaction equation

HRID 2216158 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]([C:10]1[S:11][C:12]([S:34][CH3:35])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[CH:26][C:25]=3[NH2:33])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[Br:37][CH2:38][C:39](Br)=[O:40].CCN(CC)CC.CCOC(C)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]([C:10]1[S:11][C:12]([S:34][CH3:35])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:25]([NH:33][C:39](=[O:40])[CH2:38][Br:37])=[CH:26][C:27]([O:31][CH3:32])=[CH:28][C:29]=3[CH3:30])[CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH:14]=1)=[NH:9])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 145857653tert-butyl N-[4-[3-(2-amino-4-methoxy-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857627tert-butyl N-[4-[3-[2-[(2-bromoacetyl)amino]-4-methoxy-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described for Example 234, step a, reaction of {[4-(6′-amino-4′-methoxy-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (204 mg, 0.37 mmol, as prepared in Example 198, step e), bromoacetyl bromide (39 μL, 0.45 mmol), and Et3N (77 μL, 0.56 mmol) in DCM (5 mL) afforded 170 mg (69%) of the title compound as a yellow foamy solid after chromatography (PTLC, 50% EtOAc in hexanes, 4×1000μ SiO2 plate). 1H-NMR (CDCl3; 400 MHz): δ 8.02–8.05 (m, 1H), 7.91 (s, 1H), 7.87 (t, 1H, J=1.6 Hz), 7.73 (br s, 1H), 7.63–7.67 (m, 2H), 7.45–7.49 (m, 1H), 6.69 (d, 1H, J=2.1 Hz), 3.85 (s, 3H), 3.69 and 3.74 (AB quartet, 2H, J=14.1 Hz), 2.59 (s, 3H), 2.00 (s, 3H), 1.52 (s, 9H). ESI-MS (m/z): Calcd. for C27H30BrN3O6S3: 668.0 (M+H); found: 669.6, 667.6, 570.0, 568.0 (M−Boc).

Sources & evidence

ORD record
ord-ece7fb57a9ec43daa753f21d2e68e2e3
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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