Triethylamine → HCID 24826252, compound

HRID 910948Notes

Reaction equation

HRID 910948 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([OH:20])=O)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C(N(CC)CC)C.C([Cl:36])(=O)OCC.[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH2:41]>C1COCC1>[ClH:36].[ClH:36].[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH:41][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([O:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[CH:13]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66053N,N-DimethylethylenediamineHCID 24825977HCID 24825977, compound

Product 1

HCID 24826252HCID 24826252, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid (0.1 g, 0.3055 mmol), triethylamine (0.2129 mL, 1.527 mmol) and THF (2 mL) were combined according to the method of Example 32. The reaction mixture was cooled to 0° C., ethyl carbonochloridate (0.03359 mL, 0.3513 mmol) was added, and the reaction mixture was stirred at 0° C. for 30 minutes. N1,N1-dimethylethane-1,2-diamine (0.1006 mL, 0.9164 mmol) in THF (2 mL) was added to afford N-(2-(dimethylamino)ethyl)-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzamide dihydrochloride (0.07 g, 48.23% yield) as off white solid. 1H NMR (CDCl3) δ 8.97 (bs, 1H), 8.16 (d, 1H), 7.99 (m, 2H), 7.52 (t, 1H), 7.23 (d, 1H), 6.92 (bs, 1H), 6.39 (s, 1H), 3.90 (m, 2H), 3.37 (m, 2H), 2.92 (s, 6H), 2.38 (s, 3H); Mass spectrum (esi) m/z=398 (100) (M+H).

Sources & evidence

ORD record
ord-dc2f7219af644f84a9c07cbf2c6b92db
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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