Diisopropylethylamine → HCID 53391247, compound

HRID 2408828Notes

Reaction equation

HRID 2408828 reaction equation
[O:1]=[C:2]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:20][C:21]([OH:23])=O.[CH3:24][C:25]1([CH3:32])[NH:30][CH2:29][CH2:28][NH:27][C:26]1=[O:31].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:24][C:25]1([CH3:32])[N:30]([C:21](=[O:23])[CH2:20][N:3]2[CH2:4][CH2:5][CH2:6][C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]2=[O:1])[CH2:29][CH2:28][NH:27][C:26]1=[O:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2111572-Piperazinone, 3,3-dimethyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 53391247HCID 53391247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.15 g, 0.485 mmol) and 3,3-dimethylpiperazin-2-one (CAS 22476-74-0) (0.062 g, 0.485 mmol) in dichloromethane (3 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.184, 0.485 mmol) and diisopropylethylamine (0.53 mL, 2.91 mmol). The reaction mixture was stirred at ambient temperature overnight and then concentrated followed by chromatographic purification on an Analogix silica gel column eluting with 5% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.05-8.11 (m, 1H), 7.16-7.32 (m, 10H), 4.20 (s, 2H), 3.46-3.52 (m, 2H), 3.33-3.41 (m, 2H), 3.16-3.22 (m, 2H), 2.51-2.57 (m, 2H), 1.63-1.75 (m, 2H), 1.60 (s, 6H); MS (DCI+) m/z 420 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customfollowed by chromatographic purification on an Analogix silica gel column
  3. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-b2f00e22700b442dbe2051f2c40adb03
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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