Ethanolamine → [3-(4-Fluorophenyl)(1h-indazol-5-yl)]-n-(2-hydroxyethyl)carboxamide

HRID 1273045Notes

Reaction equation

HRID 1273045 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:43]([CH2:45][NH2:46])[OH:44]>O1CCCC1.O.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH:46][CH2:45][CH2:43][OH:44])=[O:19])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 700EthanolamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 222607223-(4-Fluorophenyl)-1H-Indazole-5-Carboxylic Acid

Product 1

HCID 20789050[3-(4-Fluorophenyl)(1h-indazol-5-yl)]-n-(2-hydroxyethyl)carboxamideYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in Example 76. To a solution of 3-(4-fluorophenyl)-1H-indazole-5-carboxylic acid (0.200 g, 0.781 mmol) in tetrahydrofuran (5 mL) was added 1-hydroxybenzotriazole hydrate (0.316 g, 2.34 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.449 g, 2.34 mmol), ethanolamine (0.141 mL, 2.34 mmol) and N,N-dimethylformamide (2 mL). The solution was stirred for 16 h at room temperature. Water (40 mL) was added and the solid was filtered and dried in a vacuum oven which gave the title compound (0.161 g, 69% yield): 1H NMR (DMSO-d6) δ 13.45 (s, 1H), 8.61 (t, 1H), 8.56 (s, 1H), 8.08 (AB quartet, 2H), 7.93 (dd, 1H), 7.62 (d, 1H), 7.40 (t, 2H), 4.76 (t, 1H), 3.54 (q, 2H), 3.80 (q, 2H); ES-MS (m/z) 300 [M+1]+.

Workup

  1. customThe title compound was prepared
  2. filtrationthe solid was filtered
  3. customdried in a vacuum oven which

Sources & evidence

ORD record
ord-2abd689fc1b04623b9a3b1bd9868aec4
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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