Diisopropylethylamine → HCID 67359063, compound

HRID 1667195Notes

Reaction equation

HRID 1667195 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](=[O:24])[N:15]3[CH2:18][C:17]4([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[CH2:16]3)[C:9]2=[O:25])=[CH:4][CH:3]=1.Br[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=1.C(N(C(C)C)C(C)C)C>ClCCl>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:8]2([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](=[O:24])[N:15]3[CH2:18][C:17]4([CH2:19][CH2:20][N:21]([CH2:34][C:35]5[CH:36]=[CH:37][C:38]([C:41]([F:42])([F:43])[F:44])=[CH:39][CH:40]=5)[CH2:22][CH2:23]4)[CH2:16]3)[C:9]2=[O:25])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 53391432HCID 53391432, compound

Product 1

HCID 67359063HCID 67359063, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 3,3-bis(4-fluorophenyl)-1-(2-oxo-2-(2,7-diazaspiro[3.5]nonan-2-yl)ethyl)pyrrolidin-2-one (0.050 g, 0.114 mmol; Example 153A) and 1-(bromomethyl)-4-(trifluoromethyl)benzene (0.030 g, 0.125 mmol) in dichloromethane (0.5 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.030 mL, 0.171 mmol), and the reaction was heated to 40° C. for 1 hour. The reaction was cooled, loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences), and the title compound eluted with a gradient of 0.8% methanol/dichloromethane containing 0.2 N NH3 to 5.6% methanol/dichloromethane containing 0.2 N NH3(Flow=25 mL/minute) over 30 minutes. 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=8.1, 2H), 7.42 (d, J=8.0, 2H), 7.34-7.27 (m, 4H), 7.04-6.94 (m, 4H), 3.97 (s, 2H), 3.72 (d, J=19.3, 4H), 3.52 (dd, J=5.5, 12.0, 4H), 2.75 (t, J=6.5, 2H), 2.31 (s, 4H), 1.74 (d, J=4.9, 4H); MS (ESI+) m/z 598.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. washthe title compound eluted with a gradient of 0.8% methanol/dichloromethane containing 0.2 N NH3 to 5.6% methanol/dichloromethane containing 0.2 N NH3(Flow=25 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-22828970317a45a3b2d761ecc284b799
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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