1-Pyrrolidineethanamine → HCID 24826246, compound

HRID 910945Notes

Reaction equation

HRID 910945 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:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([OH:20])=O)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C(N(CC)CC)C.C([Cl:36])(=O)OCC.[N:37]1([CH2:42][CH2:43][NH2:44])[CH2:41][CH2:40][CH2:39][CH2:38]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:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([NH:44][CH2:43][CH2:42][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:20])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24825977HCID 24825977, compound

Product 1

HCID 24826246HCID 24826246, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the method of Example 32, 3-(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 (0.03359 mL, 0.3513 mmol), 2-(pyrrolidin-1-yl)ethanamine (0.1161 mL, 0.9164 mmol) were reacted in THF (2 mL) to provide 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide dihydrochloride (0.088 g, 57.45% yield) as an off white solid. 1H NMR (CDCl3) δ 8.88 (s, 1H), 8.17 (d, 1H), 8.02 (d, 1H), 7.96 (s, 1H), 7.54 (t, 1H), 7.24 (m, 1H), 6.76 (dd, 1H), 6.39 (s, 1H), 3.97 (m, 2H), 3.90 (m, 2H), 3.37 (m, 2H), 2.87 (m, 2H), 2.40 (d, 3H), 2.25 (m, 2H), 2.09 (m, 2H); Mass spectrum (esi) m/z=424 (100) (M+H).

Sources & evidence

ORD record
ord-510e53b25deb4cae9739509bba1eb882
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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