Trimethylsilyl isocyanate → HCID 86620397, compound

HRID 252721Notes

Reaction equation

C[Si]([N:5]=[C:6]=[O:7])(C)C.[NH2:8][C:9]1[S:10][C:11]([C:15]2[CH:16]=[C:17]([NH:22][S:23]([C:26]3[S:30][C:29]([CH3:31])=[N:28][C:27]=3[CH3:32])(=[O:25])=[O:24])[C:18]([Cl:21])=[N:19][CH:20]=2)=[C:12]([CH3:14])[N:13]=1>COCCOC>[Cl:21][C:18]1[C:17]([NH:22][S:23]([C:26]2[S:30][C:29]([CH3:31])=[N:28][C:27]=2[CH3:32])(=[O:25])=[O:24])=[CH:16][C:15]([C:11]2[S:10][C:9]([NH:8][C:6]([NH2:5])=[O:7])=[N:13][C:12]=2[CH3:14])=[CH:20][N:19]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of trimethylsilyl isocyanate (0.032 mL), N-[5-(2-amino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]-2,4-dimethylthiazole-5-sulfonamide (46 mg) and DME (1 mL) was placed in a sealed glass reaction vessel and heated to 115° C. in a microwave reactor for 18 hours. The resultant mixture was evaporated and the residue was purified by preparative HPLC on reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound as a solid (16 mg); 1H NMR Spectrum: (DMSOd6) 2.28 (s, 3H), 2.34 (s, 3H), 2.62 (s, 3H), 6.47 (br s, 2H), 7.71 (s, 1H), 8.34 (br s, 1H), 10.55 (s, 1H), 10:85 (br s, 1H); Mass Spectrum: M+H+ 459.

Workup

customwas placed in a sealed glass reaction vessel
customThe resultant mixture was evaporated
customthe residue was purified by preparative HPLC on reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent
customThe material so obtained
customwas triturated under diethyl ether

Sources & evidence

ORD record: ord-cf1ee4ec7e5448db9127aa8f7f434aa6
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868188B2

Reaction notes

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