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

HRID 2216159Notes

Reaction equation

HRID 2216159 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][CH:36]([CH3:40])[C:37](Br)=[O:38].CCN(CC)CC.CCOC(C)=O>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])[CH:36]([Br:35])[CH3:40])=[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

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 79047Propanoyl bromide, 2-bromo-HCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857656tert-butyl N-[4-[3-[2-(2-bromopropanoylamino)-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 (65 mg, 0.126 mmol, as prepared in Example 25, step c), racemic 2-bromo-propionyl bromide (19 μL, 0.189 mmol), and Et3N (52 μL, 0.378 mmol) in DCM (2 mL) afforded 55 mg (67%) of the title compound as a glassy solid after chromatography (PTLC, 10% EtOAc in DCM, 2×1500μ SiO2 plate). ESI-MS (m/z): Calcd. for C27H30BrN3O5S3: 652.0 (M+H); found: 653.6, 651.7, 553.9, 552.0 (M−Boc).

Sources & evidence

ORD record
ord-5b1ea8bf89944325b78d0cd7b2317753
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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