Diisopropylethylamine → HCID 11315482, compound

HRID 751703Notes

Reaction equation

HRID 751703 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.[Cl:27][C:28]1[CH:29]=[C:30]2[CH:36]=[C:35]([C:37](O)=[O:38])[NH:34][C:31]2=[CH:32][N:33]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[O:5]=[C:4]([N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[C@@H:3]([NH:2][C:37]([C:35]1[NH:34][C:31]2=[CH:32][N:33]=[C:28]([Cl:27])[CH:29]=[C:30]2[CH:36]=1)=[O:38])[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidHCID 67278826HCID 67278826, compound

Product 1

HCID 11315482HCID 11315482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-amino-3-pyridin-3-yl-1-pyrrolidin-1-ylpropan-1-one hydrochloride (Preparation 54, 239 mg, 0.94 mmol) in DMF (5 mL) was added DIPEA (0.60 mL, 3.28 mmol), 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 184 mg, 0.94 mmol) and TBTU (330 mg, 1.03 mmol). The reaction mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 mL) and sodium hydroxide solution (2×100 mL, 1N). The organic phase was dried (MgSO4) and evaporated to dryness give the title compound as a brown solid. δH (CD3OD): 1.74–1.94 (4H, m), 3.12–3.39 (4H, m), 3.41–3.48 (1H, m), 3.69–3.75 (1H, m), 5.07–5.12 (1H, m), 7.16 (1H, s), 7.34–7.39 (1H, m), 7.67 (1H, s), 7.79–7.83 (1H, m), 8.37–8.42 (1H, m), 8.45–8.51 (1H, m), 8.56 (1H, s); m/z (ES+)=398 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (100 mL) and sodium hydroxide solution (2×100 mL, 1N)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-386d9521beeb48409a292586917a97b5
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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