PyBOP → HCID 9849748, compound

HRID 1275187Notes

Reaction equation

HRID 1275187 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C@H:18]([CH3:27])[CH2:19][N:20]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)=[CH:15][C:14]([C:28]([CH3:33])([CH3:32])[C:29]([OH:31])=O)=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl.[CH:35]12[NH:41][CH:38]([CH2:39][CH2:40]1)[CH2:37][CH2:36]2.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(N(CC)CC)C>[CH:38]12[N:41]([C:29](=[O:31])[C:28]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[NH:10][C:9]([C:4]3[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=3)=[C:17]4[C@H:18]([CH3:27])[CH2:19][N:20]3[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]3)([CH3:33])[CH3:32])[CH:35]([CH2:40][CH2:39]1)[CH2:36][CH2:37]2

Participants

5

Reactant 3

HCID 2724699PyBOPHCID 162795037-Azabicyclo[2.2.1]heptane hydrochlorideHCID 18397034HCID 18397034, compound

Product 1

HCID 9849748HCID 9849748, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of (S)-2-(2-(3,5-dimethylphenyl)-3-[1-methyl-2(4-oxo-piperidin-1-yl)-ethyl]-1H-indol-5-yl]-2-methylpropionic acid (148 mg in 2 mL dry methylene chloride) was added 58 mg 7-aza-bicyclo[2.2.1]heptane hydrochloride followed by 0.185 mL triethylamine and 173 mg of the PyBOP reagent and the mixture stirred at room temperature. After 14 hours, the mixture was concentrated in vacuo and the residue dissolved in ethyl acetate, washed with water and brine and the organic portion dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 3:2) gave the title compound (128 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialthe organic portion dried over sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate:hexane, 3:2)

Sources & evidence

ORD record
ord-0050987d8edd4629a9b0a80cd206316b
Source dataset
uspto-grants-2000_12
Patent number
US06159989

Reaction notes

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