Ethanolamine → HCID 58902306, compound

HRID 1640208Notes

Reaction equation

HRID 1640208 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]#[N:32])[CH:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:33]([CH2:35]N)[OH:34].CCN(C(C)C)C(C)C>CCO>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]5[O:34][CH2:33][CH2:35][N:32]=5)[CH:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 58902223HCID 58902223, compound

Product 1

HCID 58902306HCID 58902306, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-tert-butylphenyl)-7-[(2-cyanopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxamide (1.184 g, 2.78 mmol) in EtOH (30 mL) was added ethanolamine (1.00 mL, 16.6 mmol) and DIPEA (1.00 mL, 5.74 mmol). The reaction mixture was allowed to stir at 100° C. for 12 h. The mixture was concentrated and the residue was diluted with water and EtOAc. The solution was extracted with EtOAc and the organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-(3-tert-butylphenyl)-7-{[2-(4,5-dihydro-1,3-oxazol-2-yl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide I-305 (1.069 g, 82%) as a white solid. 1H NMR (400 MHz, d6-DMSO, HCl salt) δ: 9.97 (s, 1H), 9.02 (t, 1H), 8.52 (d, 1H), 7.66-7.62 (m, 1H), 7.52-7.47 (m, 1H), 7.40-7.36 (m, 1H), 7.26-7.17 (m, 3H), 7.08-6.94 (m, 3H), 3.72 (t, 2H), 3.59 (q, 2H), 2.97-2.71 (m, 5H), 2.15-2.06 (m, 1H), 1.85-1.74 (m, 1H), and 1.25 (s, 9H). LCMS: (FA) ES+470.4, ES−468.2.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with water and EtOAc
  3. extractionThe solution was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-007f3e7137d5442a98592b132619d22d
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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