Water → Racemic-(trans)-2-[4-({[4-(2-pyridinyl)phenyl]methyl}amino)phenyl]cyclopropanecarboxamide

HRID 1173021Notes

Reaction equation

HRID 1173021 reaction equation
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][NH:38][C:39]2[CH:44]=[CH:43][C:42]([C@@H:45]3[CH2:47][C@H:46]3[C:48]([OH:50])=O)=[CH:41][CH:40]=2)=[CH:33][CH:32]=1.[OH-].[NH4+].O>CN(C=O)C.ClCCl>[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:32]=[CH:33][C:34]([CH2:37][NH:38][C:39]2[CH:40]=[CH:41][C:42]([C@@H:45]3[CH2:47][C@H:46]3[C:48]([NH2:2])=[O:50])=[CH:43][CH:44]=2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11371354Racemic-(trans)-2-[4-({[4-(2-pyridinyl)phenyl]methyl}amino)phenyl]cyclopropanecarboxylic acid

Product 1

HCID 11393761Racemic-(trans)-2-[4-({[4-(2-pyridinyl)phenyl]methyl}amino)phenyl]cyclopropanecarboxamideYield 38.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

HATU (0.11 g, 0.29 mmol) and racemic-(trans)-2-[4-({[4-(2-pyridinyl)phenyl]methyl}amino)phenyl]cyclopropanecarboxylic acid (I-2c) (0.077 g, 0.22 mmol) in DMF (5 mL) were stirred at RT for 10 min, then ammonium hydroxide (2 mL) was added. The solution was stirred at RT for 16 h, then water (50 mL) and dichloromethane (50 mL) were added and the organic layer was separated, washed with water (50 mL), dried over Na2SO4, filtered and concentrated to give the title compound as a white powder (0.029 g, 38%). 1H NMR (400 MHz, DMSO) δ8.64 (d, J=3.8 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.92 (d, J=8.0 Hz, 1H), 7.86 (t, J=7.9 Hz, 1H), 7.49 (s, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.33 (t, J=5.3 Hz, 1H), 6.81-6.79 (m, 3H), 6.50 (d, J=8.4 Hz, 2H), 6.19 (t, J=6.1 HZ, 1H), 4.30 (d, J=6.0 Hz, 2H), 2.05-2.00 (m, 1H), 1.64-1.60 (m, 1H), 1.20-1.15 (m, 1H), 1.03-0.98 (m, 1H). ES-MS m/z 344.2 (MH+).

Workup

  1. customthe organic layer was separated
  2. washwashed with water (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-86bbc31c1ce34f9393c7625ec533ff9b
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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