Diisopropylethylamine → HCID 86727074, compound

HRID 1502025Notes

Reaction equation

HRID 1502025 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:6]([CH3:13])=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:4].[C:14]([N:21]1[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:27][OH:28])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(C(C)C)C(C)C>C1COCC1>[C:8]([C:7]1[C:6]([CH3:13])=[C:5]([C:3](=[O:4])[CH2:2][N:24]2[CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:22][C@@H:23]2[CH2:27][OH:28])[CH:12]=[CH:11][CH:10]=1)#[N:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 86727073HCID 86727073, compound

Product 1

HCID 86727074HCID 86727074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(chloroacetyl)-2-methylbenzonitrile (1.7 g, 8.8 mmol) in THF (17.6 mL) was added (R)-4-N-boc-2-hydroxymethyl-piperazine (2.279 g, 10.54 mmol) and DIPEA (3.07 mL, 17.56 mmol) at rt. The reaction mixture was stirred at rt over the weekend. After concentration, the residue was partitioned between EtOAc and aqueous NaHCO3 (saturated). The aqueous layer was extracted with EtOAc (2×). The combined organic phase was washed with brine, dried over anhydrous MgSO4, and filtered. Concentration was followed by purification by prep TLC (silica gel; 10% MeOH/DCM) to give the title compound: LC/MS (M+1)+=374.14

Workup

  1. concentrationAfter concentration
  2. customthe residue was partitioned between EtOAc and aqueous NaHCO3 (saturated)
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationConcentration
  8. customwas followed by purification by prep TLC (silica gel; 10% MeOH/DCM)

Sources & evidence

ORD record
ord-dffef0095e204fbe93c7a02899456426
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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