Triethylamine → HCID 86634723, compound

HRID 910944Notes

Reaction equation

HRID 910944 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.[CH:37]([NH:40][CH2:41][CH2:42][NH2:43])([CH3:39])[CH3:38]>C1COCC1>[ClH:36].[ClH:36].[CH:37]([NH:40][CH2:41][CH2:42][NH:43][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([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)[CH:16]=1)([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 88098N-IsopropylethylenediamineHCID 24825977HCID 24825977, compound

Product 1

HCID 86634723HCID 86634723, compoundYield 74%

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), N1-isopropylethane-1,2-diamine (0.1143 mL, 0.9164 mmol) were reacted in THF (2 mL) to provide N-(2-(isopropylamino)ethyl)-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzamide dihydrochloride (0.063 g, 39.59% yield) as a light yellow solid. 1H NMR (CDCl3) δ 9.51 (bs, 1H), 8.74 (s, 1H), 8.15 (d, 1H), 7.92 (d, 1H), 7.81 (s, 1H), 7.49 (t, 1H), 7.22 (d, 1H), 6.83 (d, 1H), 6.44 (s, 1H), 3.92 (m, 2H), 3.24 (m, 2H), 3.12 (m, 1H), 2.42 (s, 3H), 1.46 (d, 6H); Mass spectrum (esi) m/z=412 (100) (M+H).

Sources & evidence

ORD record
ord-17aad60794da461296b22c6ed7ae93b1
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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