Diisopropylethylamine → HCID 137329924, compound

HRID 1715418Notes

Reaction equation

HRID 1715418 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:23]([SiH2:27][O:28][C:29]([CH3:41])([CH3:40])[C:30]1[CH:31]=[C:32]([CH2:37][CH2:38][NH2:39])[CH:33]=[CH:34][C:35]=1[Cl:36])([CH3:26])([CH3:25])[CH3:24].[F:42][C:43]([F:49])([F:48])[CH2:44][C:45](O)=[O:46].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:23]([SiH2:27][O:28][C:29]([CH3:41])([CH3:40])[C:30]1[CH:31]=[C:32]([CH2:37][CH2:38][NH:39][C:45](=[O:46])[CH2:44][C:43]([F:49])([F:48])[F:42])[CH:33]=[CH:34][C:35]=1[Cl:36])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27779723,3,3-Trifluoropropionic acidHCID 137329923HCID 137329923, compound

Product 1

HCID 137329924HCID 137329924, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TBTU (2.09 g, 6.50 mmol) was added to a sol. of 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethylamine (1.30 g, 4.33 mmol), 3,3,3-trifluoropropionic acid (0.574 mL, 6.50 mmol) and DIPEA (2.97 mL, 17.3 mmol) in CH2Cl2 (43 mL). The mixture was stirred for 1 h, and CH2Cl2 was added. The mixture was washed with aq. sat. NH4Cl, aq. 10% Na2CO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 60:40) yielded the title compound (500 mg, 28%). LC-MS: tR=1.12 min; ES+: 410.14.

Workup

  1. washThe mixture was washed with aq. sat. NH4Cl, aq. 10% Na2CO3 and brine
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 60:40)

Sources & evidence

ORD record
ord-e3eeba6150b34a8caf8bc57c8b261543
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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