Triethylamine → HCID 24826151, compound

HRID 910939Notes

Reaction equation

HRID 910939 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.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25].C([Cl:36])(=O)OCC.[N:37]1CCCC=1CCN>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:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17]([NH:37][CH2:25][CH2:24][N:26]3[CH2:29][CH2:30][CH2:28][CH2:27]3)=[O:19])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15909175HCID 15909175, compoundHCID 24825978HCID 24825978, compound

Product 1

HCID 24826151HCID 24826151, compoundYield 149.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the method of Example 32, 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid (0.100 g, 0.3055 mmol), triethylamine (0.2129 mL, 1.527 mmol), ethyl carbonochloridate (0.03213 mL, 0.3360 mmol), 1-pyrroline ethanamine (0.1161 mL, 0.9164 mmol) in THF (2 mL) were reacted to provide 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide dihydrochloride (0.125 g, 81.60% yield) as off white solid. 1H NMR (DMSO) δ 8.616 (t, 1H), 8.20 (d, 1H), 7.77 (dd, 1H), 7.61 (dt, 1H), 7.41 (dt, 1H), 7.26 (d, 1H), 6.62 (s, 1H), 6.58 (m, 1H), 6.56 (m, 1H), 3.51 (m, 4H), 3.17 (quart, 2H), 2.92 (m, 2H), 2.23 (d, 3H), 1.93 (m, 2H), 1.82 (m, 2H); Mass spectrum (esi) m/z=424 (100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4578e8cd0710417882bf6676f0224f5b
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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