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Diisopropylethylamine → 2-[5-Chloro-3-(isopropylamino)-2-oxo-6-phenylpyrazin-1(2H)-yl]-N-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)acetamide

HRID 1809047
Notes
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Reaction equation

HRID 1809047 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:19][CH:20]([CH3:22])[CH3:21])[C:5](=[O:18])[N:6]([CH2:14][C:15]([OH:17])=O)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:23][C:24]1[CH:25]=[C:26]2[CH2:41][C:31]3([C:39]4[C:34](=[N:35][CH:36]=[CH:37][CH:38]=4)[NH:33][C:32]3=[O:40])[CH2:30][C:27]2=[N:28][CH:29]=1.C1CN(C(Cl)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:19][CH:20]([CH3:22])[CH3:21])[C:5](=[O:18])[N:6]([CH2:14][C:15]([NH:23][C:24]2[CH:25]=[C:26]3[CH2:41][C:31]4([C:39]5[C:34](=[N:35][CH:36]=[CH:37][CH:38]=5)[NH:33][C:32]4=[O:40])[CH2:30][C:27]3=[N:28][CH:29]=2)=[O:17])[C:7]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27366521-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium HexafluorophosphateHCID 10969299[5-chloro-3-(isopropylamino)-2-oxo-6-phenylpyrazin-1(2H)-yl]acetic acidHCID 579740903-amino-5,7-dihydrospiro[cyclopenta-[b]pyridin-6.3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 45138838
2-[5-Chloro-3-(isopropylamino)-2-oxo-6-phenylpyrazin-1(2H)-yl]-N-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [5-chloro-3-(isopropylamino)-2-oxo-6-phenylpyrazin-1(2H)-yl]acetic acid (74 mg, 0.23 mmol) [Parlow et al. (2003) J. Med. Chem. 46, 4050], (±)-3-amino-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (71 mg, 0.28 mmol) [Wood et al. US 2007/265225], N,N,N′,N′-bis(tetramethylene)chloroformamidinium hexafluorophosphate (153 mg, 0.46 mmol), and N,N-diisopropylethylamine (0.20 mL, 1.15 mmol) in THF (2 mL) is stirred at ambient temperature for 18 h. The reaction mixture is purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions are combined and made basic with saturated aqueous NaHCO3. The resulting mixture is extracted with EtOAc (3×20 mL), and the combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound.

Workup

  1. customThe reaction mixture is purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. extractionThe resulting mixture is extracted with EtOAc (3×20 mL)
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ac01cabd5ec478996340b59efd73e28
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362005B2

Reaction notes

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