Cesium carbonate → HCID 131723712, compound

HRID 2298664Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]=[N:10][C:11]1[S:12][C:13]([S:29][CH3:30])=[C:14]([C:16]2[N:17]=[C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=3)[S:19][CH:20]=2)[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:32].[Cs+].[Cs+].Br[CH2:38][C:39]([NH2:41])=[O:40]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]=[N:10][C:11]1[S:12][C:13]([S:29][CH3:30])=[C:14]([C:16]2[N:17]=[C:18]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([O:32][CH2:38][C:39](=[O:40])[NH2:41])[CH:27]=3)[S:19][CH:20]=2)[CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 58 °C

Procedure

To stirring solution of (tert-butoxy)-N-[(4-{2-[(4-hydroxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthio(2-thienyl))iminomethyl]carboxamide (65 mg, 0.14 mmol) in 1.5 mL of DMF was added sequentially Cs2CO3 (1.5 equiv, 60.1 mg, Aldrich Chemicals, Milwaukee, Wis.), bromoacetamide (1.2 equiv, 20.4 mg, Aldrich Chemicals, Milwaukee, Wis.), and a catalytic amount of KI. The reaction was warmed to 58° C. in an oil bath, stirred for 48 h, at which time another 0.6 equiv of bromoacetamide was added. Stirring was continued for another 24 h, at which time the reaction was filtered and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (50% ethyl acetate-hexanes) to give 9 mg (12% yield) of (tert-butoxy)-N-{[4-(2-{[3-(carbamoylmethoxy)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthio(2-thienyl)]iminomethyl}carboxamide. Mass Spectrum (ESI) m/z calcd. for C22H25N5O4S3, 519.7 (M+H), found 519.7, 420.7 [—C(O)OC(CH3)3].

Workup

additionwas added
filtrationthe reaction was filtered
concentrationconcentrated in vacuo
customThe residue was purified by preparative thin layer chromatography (50% ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-8e83c5f1cc0f4b09ac0f68438c1e60d6
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492403B1

Reaction notes

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