Triethylamine → HCID 87076695, compound

HRID 910942Notes

Reaction equation

HRID 910942 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.[CH3:37][NH:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42]>C1COCC1>[ClH:36].[ClH:36].[CH3:42][N:41]([CH3:43])[CH2:40][CH2:39][N:38]([CH3:37])[C:17](=[O:19])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[O:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 24825978HCID 24825978, compound

Product 1

HCID 87076695HCID 87076695, compoundYield 82.3%

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), N,N,N-trimethylethylenediamine (0.1191 mL, 0.9164 mmol) in THF (2 mL) were reacted to provide N-(2-(dimethyl-amino)ethyl)-N-methyl-2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzamide dihydrochloride (0.067 g, 44.82% yield) as off white solid. 1H NMR (CDCl3) δ 8.20 (d, 1H), 7.57 (d, 1H), 7.50 (t, 1H), 7.38 (t, 1H), 7.13 (d, 1H), 6.79 (s, 1H), 6.59 (dd, 1H), 6.40 (d, 1H), 3.97 (m, 2H), 3.17 (m, 2H), 3.03 (s, 3H), 2.87 (s, 6H), 2.41 (s, 3H); Mass spectrum (esi) m/z=412 (100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9fba864dcb5243a29fffd17c6cfba673
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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