Triethylamine → HCID 15907678, compound

HRID 1872918Notes

Reaction equation

HRID 1872918 reaction equation
C1CN([P+](ON2N=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:34]([O:41][CH2:42][C@H:43]([C:45]1[C:53]2[C:48](=[N:49][CH:50]=[C:51]([C:54]([CH3:59])([CH3:58])[C:55](O)=[O:56])[CH:52]=2)[NH:47][C:46]=1[C:60]1[CH:65]=[C:64]([CH3:66])[CH:63]=[C:62]([CH3:67])[CH:61]=1)[CH3:44])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl.C12NC(CC1)CC2.C(N(CC)CC)C.O.[Cl-].[Na+].O>ClCCl>[CH:20]12[N:25]([C:55](=[O:56])[C:54]([C:51]3[CH:52]=[C:53]4[C:45]([C@H:43]([CH3:44])[CH2:42][O:41][CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[C:46]([C:60]5[CH:65]=[C:64]([CH3:66])[CH:63]=[C:62]([CH3:67])[CH:61]=5)[NH:47][C:48]4=[N:49][CH:50]=3)([CH3:59])[CH3:58])[CH:23]([CH2:24][CH2:19]1)[CH2:22][CH2:21]2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 2724699PyBOPHCID 15887219(S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acidHCID 162795037-Azabicyclo[2.2.1]heptane hydrochlorideHCID 23713072Sodium chloride dihydrate

Product 1

HCID 15907678HCID 15907678, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBOP (1.51 g, 2.89 mmol) was added to a stirred mixture of the crude (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (1.20 g, 2.63 mmol), 7-azabicyclo[2.2.1]heptane hydrochloride (0.70 g, 5.26 mmol) and triethylamine (1.47 mL, 10.5 mmol) in dichloromethane (26 mL) at ambient temperature. After approximately 12 h, the reaction mixture was poured into water/brine (1:1) and extracted with ethyl acetate (×3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (gradient eluton; 60-75% ethyl acetate/hexanes as eluent) to give the title compound as a colourless foam (1.33 g).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (gradient eluton; 60-75% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-10fe1084a0f746f08e870263e5a25f13
Source dataset
uspto-grants-2000_08
Patent number
US06110931

Reaction notes

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