Tetrahydrofuran → 1-{[5-Bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-yl]carbonyl}imidazolidin-4-one

HRID 2038365Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[N:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Cl:17])[CH:11]=1.C1CN([P+](ON2N=[N:42][C:37]3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C([N:54](CC)C(C)C)(C)C.[O:60]1CC[CH2:62][CH2:61]1>>[Br:1][C:2]1[S:6][C:5]([C:7]([N:54]2[CH2:62][C:61](=[O:60])[NH:42][CH2:37]2)=[O:9])=[N:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Cl:17])[CH:11]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 81531Diisopropylethylamine

HCID 2724699PyBOP

HCID 708016435-Bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylic acid

Product 1

HCID 708015141-{[5-Bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-yl]carbonyl}imidazolidin-4-one

Procedure

190 mg of the compound from Example 6A having a purity of 86% (0.49 mmol), 107 mg (0.54 mmol) of the compound from Example 20A and 380 mg (0.73 mmol) of PyBOP are provided in 2 ml of tetrahydrofuran, and 0.27 ml (1.56 mmol) of N,N-diisopropylethylamine are added at room temperature. The reaction mixture is stirred at room temperature overnight and then purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with the addition of 0.1% formic acid). 109 mg (55% of theory) of the title compound are obtained.

Workup

custompurified by preparative HPLC (RP18 column
additionmobile phase: acetonitrile/water gradient with the addition of 0.1% formic acid)

Sources & evidence

ORD record: ord-9678981906b142198831476081167de5
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575357B2

Reaction notes

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