Triethylamine → HCID 57665511, compound

HRID 2358428Notes

Reaction equation

[NH2:1][C@@H:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=1)[CH3:3].C(N(CC)CC)C.[C:28]([C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>C(Cl)Cl>[C:28]([C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:40])[NH:1][C@@H:2]([C:4]2[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([C:15]#[C:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[CH:5]=2)[CH3:3])=[CH:34][CH:33]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

(R)—N-[4-(1-Amino-ethyl)-2-trimethylsilanylethynylphenyl]methanesulfonamide (75.0 mg, 0.242 mmol, 1 eq.) and Triethylamine (67.5 μl, 0.484 mmol, 2 eq.) were dissolved in methylene chloride. The mixture was cooled down to 0° C. 4-tert-Butylphenyl isocyanate (47.2 μl, 0.266 mmol, 1.1 eq.) was added into the reaction mixture. The reaction mixture was stirred for 40 min. A reaction solvent was removed in vacuo. The residue was purified with column chromatography (n-Hx:EA=2:1) to yield title compound (45.3 mg, 39%) as a solid.

Workup

customA reaction solvent was removed in vacuo
customThe residue was purified with column chromatography (n-Hx:EA=2:1)

Sources & evidence

ORD record: ord-4b7cf96d6b3e44428ec70b2fc7ba54df
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763657B2

Reaction notes

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