Triethylamine → HCID 178431957, compound

HRID 910943Notes

Reaction equation

HRID 910943 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:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17]([OH:19])=O)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C(N(CC)CC)C.C([Cl:36])(=O)OCC.[NH2:37][CH2:38][CH2:39][C:40]1[N:44]=[CH:43][NH:42][CH:41]=1>C1COCC1>[ClH:36].[ClH:36].[NH:42]1[CH:41]=[C:40]([CH2:39][CH2:38][NH:37][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[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)[N:44]=[CH:43]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24825978HCID 24825978, compoundHCID 178419017HCID 178419017, compound

Product 1

HCID 178431957HCID 178431957, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the method of Example 32, 2-(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 (0.03213 mL, 0.3360 mmol), and histamine (0.1019 g, 0.9164 mmol) were reacted in THF (2 mL) to provide N-(2-(1H-imidazol-4-yl)ethyl)-2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzamide dihydrochloride (0.084 g, 55.17% yield). 1H NMR (CDCl3) δ 8.38 (s, 1H), 8.08 (d, 1H), 7.76 (d, 1H), 7.51 (t, 1H), 7.39 (t, 1H), 7.06 (s, 1H), 7.02 (m, 2H), 6.89 (s, 1H), 6.55 (m, 2H), 3.81 (m, 2H), 3.16 (m, 2H), 2.45 (s, 3H); Mass spectrum (esi) m/z=421 (100) (M+H).

Sources & evidence

ORD record
ord-7a25526c07274fe8b80d2292763d4d83
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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