Triethylamine → HCID 15907678, compound

HRID 1976700Notes

Reaction equation

HRID 1976700 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 12h, the reaction mixture was poured into water/brine (1:1) and extracted with ethyl acetate (x3). 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 acetatethexanes as eluent) to give the title compound as a foam (1.33 g).

Workup

  1. extractionextracted with ethyl acetate (x3)
  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 acetatethexanes as eluent)

Sources & evidence

ORD record
ord-adb096e7f5d046bcba1b1ba39f6ec5ff
Source dataset
uspto-grants-2001_05
Patent number
US06228867B1

Reaction notes

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