Triethylamine → HCID 24826248, compound

HRID 910946Notes

Reaction equation

HRID 910946 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.[O:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45][NH2:46])[CH2:39][CH2:38]1>C1COCC1>[ClH:36].[ClH:36].[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]([NH:46][CH2:45][CH2:44][CH2:43][N:40]3[CH2:41][CH2:42][O:37][CH2:38][CH2:39]3)=[O:20])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 61055N-(3-Aminopropyl)morpholineHCID 24825977HCID 24825977, compound

Product 1

HCID 24826248HCID 24826248, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the method of Example 32, 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid (0.1 g, 0.3055 mmol), triethylamine (0.2129 mL, 1.527 mmol), ethyl carbonochloridate (0.03359 mL, 0.3513 mmol), and 3-morpholinopropan-1-amine (0.1339 mL, 0.9164 mmol) were reacted in THF (2 mL) to provide 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(3-morpholinopropyl)benzamide dihydrochloride (0.098 g, 60.33% yield) as off white solid. 1H NMR (CDCl3) δ 8.52 (s, 1H), 8.19 (d, 1H), 7.91 (d, 1H), 7.74 (s, 1H), 7.54 (t, 1H), 7.24 (d, 1H), 6.82 (dd, 1H), 6.41 (s, 1H), 4.26 (m, 2H), 3.99 (m, 2H), 3.65 (m, 2H), 3.52 (m, 2H), 3.19 (t, 2H), 2.89 (m, 2H), 2.41 (d, 3H), 2.26 (m, 2H); Mass spectrum (esi) m/z=454 (100) (M+H).

Sources & evidence

ORD record
ord-441bbe44a9d743a2bb31fb40d44149b3
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…