Diisopropylethylamine → HCID 68671249, compound

HRID 2047386Notes

Reaction equation

HRID 2047386 reaction equation
C[N:2](C(ON1N=[N:16][C:11]2C=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25](N(C(C)C)CC)(C)C.[F:34][CH:35]([F:60])[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[C:45]1[CH:46]=[C:47]([N:51]2[CH2:56][CH2:55][CH:54]([C:57](O)=[O:58])[CH2:53][CH2:52]2)[CH:48]=[CH:49][CH:50]=1>ClCCl>[NH3:2].[F:34][CH:35]([F:60])[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[C:45]1[CH:46]=[C:47]([N:51]2[CH2:52][CH2:53][CH:54]([C:57]([N:15]3[CH2:10][CH2:11][N:16]([CH3:25])[CH2:13][CH2:14]3)=[O:58])[CH2:55][CH2:56]2)[CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68670594HCID 68670594, compound

Product 2

HCID 222AmmoniaHCID 68671249HCID 68671249, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

HATU (0.11 g, 0.30 mmol) and diisopropylethylamine (DIPEA) (0.09 mL, 0.54 mmol) were added to a suspension of 1-[3-(1-Difluoromethyl-1H-benzoimidazol-2-yl)-phenyl]piperidine-4-carboxylic acid (0.10 g, 0.27 mmol) in dichloromethane at room temperature. Reaction was heated at 35° C. overnight. Reaction was cooled to room temperature and washed with saturated Na2CO3 solution (2×4 mL) and with water (1×3 mL) The organic layer was concentrated under reduced pressure and crude was purified by flash chromatography (eluent: cyclohexane:AcOEt gradient from cyclohexane 1:AcOEt 1 to 100% AcOEt and finally with AcOEt: 2.0 N ammonia in methanol 5:1) to afford 0.025 g of the title compound (20%).

Workup

  1. customReaction
  2. customReaction
  3. temperaturewas cooled to room temperature
  4. washwashed with saturated Na2CO3 solution (2×4 mL) and with water (1×3 mL) The organic layer
  5. concentrationwas concentrated under reduced pressure and crude
  6. customwas purified by flash chromatography (eluent

Sources & evidence

ORD record
ord-fe281d5cd07645379bc1b41a64abcbfb
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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