Diisobutylamine → (S)-1-(N,N-Diisobutylamino)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo [2,3-b]pyridin-5-yl]-2-methylpropan-1-one

HRID 1602991Notes

Reaction equation

HRID 1602991 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=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.[CH2:68]([NH:72][CH2:73][CH:74]([CH3:76])[CH3:75])[CH:69]([CH3:71])[CH3:70].C(N(CC)CC)C>C(Cl)Cl>[CH2:68]([N:72]([C:55](=[O:56])[C:54]([C:51]1[CH:52]=[C:53]2[C:45]([C@H:43]([CH3:44])[CH2:42][O:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:46]([C:60]3[CH:65]=[C:64]([CH3:66])[CH:63]=[C:62]([CH3:67])[CH:61]=3)[NH:47][C:48]2=[N:49][CH:50]=1)([CH3:59])[CH3:58])[CH2:73][CH:74]([CH3:76])[CH3:75])[CH:69]([CH3:71])[CH3:70]

Participants

6

Reactant 4

HCID 8085DiisobutylamineHCID 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 acid

Product 1

HCID 15887220(S)-1-(N,N-Diisobutylamino)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo [2,3-b]pyridin-5-yl]-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBOP is added to a stirred mixture of (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo-[2,3-b]pyridin-5-yl]-2-methylpropanoic acid, diisobutylamine and triethylamine in CH2Cl2 at ambient temperature. After approximately 12 h, the reaction mixture is poured into waterlbrine (1:1) and extracted with ethyl acetate. The combined organic extract is washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica gel (gradient elution; 60-75% ethyl acetate/hexanes as eluent) to give the title compound.

Workup

  1. additionthe reaction mixture is poured into waterlbrine (1:1)
  2. extractionextracted with ethyl acetate
  3. extractionThe combined organic extract
  4. washis washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography on silica gel (gradient elution; 60-75% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-d7511d7755054608a38248963a8ced3c
Source dataset
uspto-grants-1999_11
Patent number
US05985892

Reaction notes

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