Triethylamine → HCID 86620403, compound

HRID 252727Notes

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C[C:19]1[S:20]C(C(O)=O)=[C:22](C)[N:23]=1.C([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.[NH2:35][C:36]1[CH:37]=[C:38]([C:43]2[S:47][C:46]([NH:48][C:49](=[O:51])[CH3:50])=[N:45][C:44]=2[CH3:52])[CH:39]=[N:40][C:41]=1[Cl:42]>O1CCOCC1.C1(C)C=CC=CC=1>[Cl:42][C:41]1[N:40]=[CH:39][C:38]([C:43]2[S:47][C:46]([NH:48][C:49](=[O:51])[CH3:50])=[N:45][C:44]=2[CH3:52])=[CH:37][C:36]=1[NH:35][C:22]([NH:23][C:19]1[S:20][C:31]([CH3:32])=[N:30][C:33]=1[CH3:34])=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

Diphenylphosphoryl azide (0.228 mL) was added to a stirred mixture of 2,4-dimethylthiazole-5-carboxylic acid (137 mg), triethylamine (0.148 mL) and toluene (3 mL) and the resultant mixture was heated to 100° C. for 1 hour. N-[5-(5-Amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (100 mg) was added followed by 1,4-dioxane (3 mL) and the resultant solution was stirred and heated to 100° C. for 2 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC. There was thus obtained the title compound as a white solid (69 mg, 45%); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.27 (s, 3H), 2.39 (s, 3H), 2.54 (s, 3H), 8.17 (s, 1H), 8.65 (s, 1H), 8.82 (s, 1H), 9.75 (s, 1H); Mass Spectrum: M+H+ 437.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated by evaporation
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-e15d81bdbaa849f08fdd32ffafc74c8e
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868188B2

Reaction notes

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