Diisopropylethylamine → HCID 67774194, compound

HRID 1808830Notes

Reaction equation

HRID 1808830 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[C:43]([O:47][C@H:48]([CH3:58])[C@H:49]([NH:56][CH3:57])[CH2:50][N:51]1[CH2:55][CH2:54][CH2:53][CH2:52]1)([CH3:46])([CH3:45])[CH3:44]>C(Cl)Cl>[C:43]([O:47][C@H:48]([CH3:58])[C@H:49]([N:56]([CH3:57])[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH3:11])[CH:4]=1)[CH2:50][N:51]1[CH2:55][CH2:54][CH2:53][CH2:52]1)([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2428284-Fluoro-3-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67774532HCID 67774532, compound

Product 1

HCID 67774194HCID 67774194, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluoro-3-methylbenzoic acid (101 mg, 0.66 mmol), TBTU (232 mg, 0.72 mmol) and DIPEA (0.172 mL, 0.99 mmol) was stirred in DCM (2 mL) for 1 h. (2R,3R)-3-tert-butoxy-N-methyl-1-(pyrrolidin-1-yl)butan-2-amine (Compound M7) (150 mg, 0.66 mmol) was added and the resultant mixture was stirred at rt overnight. The reaction mixture was washed with NaHCO3 (8% aq., 2 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (43 mg, 18%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.94, 1.05-1.15, 1.55-1.72, 2.20, 2.21-2.28, 2.31-2.45, 2.60-2.66, 2.77, 2.83, 2.90, 3.27, 3.44-3.50, 3.70-3.77, 3.87-3.93, 4.51-4.58, 7.08-7.22, 7.23-7.28, 7.37.

Workup

  1. additionwas added
  2. washThe reaction mixture was washed with NaHCO3 (8% aq., 2 mL)
  3. filtrationfiltered through a phase separator
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-200cf2ade5334fa3b034ae9c4fb68890
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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