Ethylenediamine → HCID 23585426, compound

HRID 1640172Notes

Reaction equation

HRID 1640172 reaction equation
C1C2C(=CC=CC=2)C[N:2]1[CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:22][C:23]([CH:25]2[CH2:34][C:33]3[CH:32]=[C:31]([O:35][C:36]4[CH:41]=[CH:40][N:39]=[C:38]([C:42]([NH:44][CH3:45])=[O:43])[CH:37]=4)[CH:30]=[CH:29][C:28]=3[CH2:27][CH2:26]2)=[O:24])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.C(N)CN>CCOC(C)=O.O>[NH2:2][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:22][C:23]([CH:25]2[CH2:34][C:33]3[CH:32]=[C:31]([O:35][C:36]4[CH:41]=[CH:40][N:39]=[C:38]([C:42]([NH:44][CH3:45])=[O:43])[CH:37]=4)[CH:30]=[CH:29][C:28]=3[CH2:27][CH2:26]2)=[O:24])[CH:15]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:17]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 66721518HCID 66721518, compound

Product 1

HCID 23585426HCID 23585426, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{[7-({[3-[2-(1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(trifluoromethyl)phenyl]amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide (0.158 g, 0.25 mmol) and ethane-1,2-diamine (2 mL) was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc and water. The solution was extracted with EtOAc. The combined organic solutions were washed with brine and concentrated to give a white solid. The residue was purified by column chromatography to give 4-{[7-({[3-(2-aminoethyl)-5-(trifluoromethyl)phenyl]-amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide (I-47, 137 mg, 29%) as the formate salt. 1H NMR (300 MHz, CD3OD): δ 8.44 (d, 1H), 8.42 (s, 1H), 7.91 (s, 1H), 7.78 (s, 1H), 7.51 (s, 1H), 7.34 (s, 1H), 7.24-7.21 (m, 1H), 7.07-7.04 (m, 1H), 6.92-6.89 (m, 1H), 3.24-3.19 (m, 2H), 3.10-2.78 (m, 9H), 2.56-2.13 (m, 1H), and 2.03-1.84 (m, 2H).

Workup

  1. extractionThe solution was extracted with EtOAc
  2. washThe combined organic solutions were washed with brine
  3. concentrationconcentrated
  4. customto give a white solid
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a257cba1837c458da62b28e52b27b950
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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