1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69063750, compound

HRID 1432381Notes

Reaction equation

HRID 1432381 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[N:3]=1.[NH2:24][C@@H:25]([CH2:29][OH:30])[CH:26]([CH3:28])[CH3:27].C1CCN2C(=NCCC2)CC1>CN1C(=O)CCC1.O>[CH:11]([N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH:24][CH:25]([CH:26]([CH3:28])[CH3:27])[CH2:29][OH:30])=[N:3][C:4]=2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6950587D-ValinolHCID 17954008HCID 17954008, compound

Product 1

HCID 69063750HCID 69063750, compoundYield 3.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(2-Chloro-9-isopropyl-9H-purin-6-yl)-(3-nitro-phenyl)-amine (333 mg, 1 mmol), D-valinol (310 mg, 3.0 mmol), and DBU (457 mg, 3.0 mmol) were stirred in NMP (5 mL) overnight at 150° C. under N2. After cooling, the mixture was diluted with H2O (40 mL) and was extracted with CH2Cl2 (3×25 mL). The combined extracts were washed with brine, treated with decolourising charcoal and MgSO4, filtered, and evaporated. The residue was redissolved in DMSO/H2O and chromatographed (Vydac 218TP1022; 9 mL/min, 27.5-37.5% MeCN in 0.1% aq CF3COOH over 40 min). Appropriate peak fractions were pooled and lyophilized to afford the title compound as an orange solid (12.3 mg). Anal. RP-HPLC (Vydac 218TP54; 1 mL/min): tR=15.8 min (27.5-37.5% MeCN in 0.1% aq CF3COOH over 20 min); purity>95% (λ=214 nm). DE-MALDI-TOF MS: [M+H]+=398.5 (C19H25N7O3=399.5).

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with CH2Cl2 (3×25 mL)
  3. washThe combined extracts were washed with brine
  4. additiontreated with decolourising charcoal and MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was redissolved in DMSO/H2O
  8. customchromatographed (Vydac 218TP1022; 9 mL/min, 27.5-37.5% MeCN in 0.1% aq CF3COOH over 40 min)

Sources & evidence

ORD record
ord-ca0d3a9a503f4c878782411ca0f7bb88
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

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