Ethanolamine → HCID 67976356, compound

HRID 1502335Notes

Reaction equation

HRID 1502335 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:38][CH2:39][CH2:40][OH:41]>[Cu]I>[OH:41][CH2:40][CH2:39][NH:38][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 67974626N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide

Product 1

HCID 67976356HCID 67976356, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
130 °C

Procedure

N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (150 mg, 0.51 mmol), copper(I) iodide (96 mg, 0.51 mmol), 1,10-phenanthroline (100 mg, 0.51 mmol) and cesium carbonate (216 mg, 0.66 mmol) were combined in a stainless steel container with 2-aminoethanol (3.0 mL). The resulting mixture was stirred at 120-140° C. for 12 hours under nitrogen. The reaction mixture was concentrated and purified via TLC to afford the desired product (23.4 mg, 17%). LCMS (ESI): RT (Min)=0.959, M+H+=271.8, method=A; 1H NMR (400 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.75 (s, 1H), 8.19 (s, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 6.77 (s, 1H), 6.00 (s, 1H), 4.74 (s, 1H), 3.61 (d, J=5.6 Hz, 2H), 3.17 (d, J=4.8 Hz, 2H), 1.99-1.95 (m, 1H), 0.79-0.75 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via TLC

Sources & evidence

ORD record
ord-1d8ee7af7b2c47d8b1cfa24c16b3edf9
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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