2-Methoxyethylamine → HCID 86624705, compound

HRID 604920Notes

Reaction equation

HRID 604920 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:20][C:21]2[S:22][C:23]([CH:26]=O)=[CH:24][N:25]=2)[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1.O1CCCC1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:26][C:23]1[S:22][C:21]([NH:20][C:10]2[CH:11]=[CH:12][C:13]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]3)=[C:8]([O:7][CH3:6])[CH:9]=2)=[N:25][CH:24]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 8028TetrahydrofuranHCID 86624700HCID 86624700, compound

Product 1

HCID 86624705HCID 86624705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in analogy to example 57 from 14 mg (0.19 mmol) 2-methoxyethylamine and 65 mg (0.21 mmol) 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-5-carbaldehyde using a solvent mixture of tetrahydrofurane (2 ml), and methylene chloride (1 ml). The reaction was not complete and the same amount of reagent was added like in example 57. The crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 47 mg (54%) {5-[(2-methoxy-ethylamino)-methyl]-thiazol-2-yl}-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow oil. MS ISP (m/e): 374.2 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=7.64 (s, 1H), 7.26 (s, 1H), 7.18 (d, 1H), 7.12 (s, 1H), 6.95 (d, 1H), 6.87 (s, 1H), 3.93 (s, 2H), 3.85 (s, 3H), 3.51 (t, 2H), 3.36 (s, 3H), 2.83 (t, 2H), 2.30 (s, 3H).

Workup

  1. additionthe same amount of reagent was added like in example 57
  2. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 47 mg (54%) {5-[(2-methoxy-ethylamino)-methyl]-thiazol-2-yl}-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow oil

Sources & evidence

ORD record
ord-e5f859b35f274801b543f955142765da
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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