Triethylamine → HCID 18713523, compound

HRID 279229Notes

Reaction equation

HRID 279229 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:14]([N:16]2[CH2:20][C@@H:19]([CH:21]3[CH2:23][CH2:22]3)[C@H:18]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH2:17]2)=[O:15])[CH:7]=[CH:6]1.C(N(CC)CC)C.[CH3:45][C:46](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:47]>C(Cl)Cl>[C:46]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:14]([N:16]2[CH2:20][C@@H:19]([CH:21]3[CH2:23][CH2:22]3)[C@H:18]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH2:17]2)=[O:15])[CH:7]=[CH:6]1)(=[O:47])[CH3:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 18713524HCID 18713524, compound

Product 1

HCID 18713523HCID 18713523, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.02 g (0.04 mmol) of 1-(N-(3-aminopropyl)-7-indolecarbonyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine, 0.025 mL (0.18 mmol) of triethylamine and 0.015 mL (0.16 mmol) of acetic anydride in 2 mL of CH2Cl2 was stirred for 12 h at rt. The reaction mixture was partitioned between EtOAc and water. The organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:1) to give 17 mg of the title compound. Mass Spectrum (EI) m/e 545 (M+1).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, acetone:hexanes, 1:1)

Sources & evidence

ORD record
ord-a2a41845ea5a4cb8b9b8f3a82006b094
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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