Triethylamine → HCID 86634722, compound

HRID 910941Notes

Reaction equation

HRID 910941 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.[CH2:37]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH3:38]>C1COCC1>[ClH:36].[ClH:36].[CH2:37]([N:39]1[CH2:44][CH2:43][N:42]([C:17]([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)=[O:19])[CH2:41][CH2:40]1)[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 791961-EthylpiperazineHCID 24825978HCID 24825978, compound

Product 1

HCID 86634722HCID 86634722, compoundYield 59.9%

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), 1-ethylpiperazine (0.1164 mL, 0.9164 mmol) in THF (2 mL) were reacted to provide (4-ethylpiperazin-1-yl)(2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenyl)methanone dihydrochloride (0.05 g, 32.64% yield). 1H NMR (DMSO) δ 8.18 (d, 1H), 7.6859 (dt, 1H), 7.54 (d, 1H), 7.42 (t, 1H), 7.29 (d, 1H), 6.59 (m, 2H), 6.56 (m, 1H), 3.35-3.63 (m, 4H), 3.12 (m, 2H), 2.50 (m, 4H, under DMSO), 2.22 (d, 3H), 1.22 (t, 2H); Mass spectrum (esi) m/z=424(100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3ea870a6b00045c6a4d0696170cc3a82
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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