Triethylamine → HCID 24826153, compound

HRID 910940Notes

Reaction equation

HRID 910940 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][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]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:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17]([NH:37][CH2:38][CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[O:19])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 61055N-(3-Aminopropyl)morpholineHCID 24825978HCID 24825978, compound

Product 1

HCID 24826153HCID 24826153, compoundYield 149.2%

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), 4-(3-aminopropyl)morpholine (0.1339 mL, 0.9164 mmol) in THF (2 mL) were reacted to provide 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(3-morpholinopropyl)benzamide dihydrochloride (0.132 g, 81.26% yield) as an off white solid. 1H NMR (DMSO) δ 8.44 (t, 1H), 8.18 (d, 1H), 7.68 (dd, 1H), 7.59 (dt, 1H), 7.40 (dt, 1H), 7.26 (d, 1H), 6.57 (s, 1H), 6.54 (d, 1H), 6.50 (dd, 1H), 3.89 (m, 2H), 3.29 (m, 2H), 3.20 (quart; 2H), 2.96 (m, 4H), 2.49 (m, 2H, under DMSO) 2.22 (d, 3H), 1.77 (m, 2H); Mass spectrum (esi) m/z=454(100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cceb925088c34b1399f20e0d518eb7a3
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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