Triethylamine → HCID 9847558, compound

HRID 1172570Notes

Reaction equation

HRID 1172570 reaction equation
[CH:1]12[CH2:8][N:7]([C:9](OC(C)(C)C)=O)[CH2:6][CH:5]1[CH2:4][CH2:3][NH:2]2.[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH2:19]Cl.CCN(CC)CC.[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38]1[N:51]=[C:41]2[N:42]=C(S(C)(=O)=O)[N:44]=[C:45]([NH2:46])[N:40]2[N:39]=1>CC#N.CCOC(C)=O>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH2:19][N:2]1[CH2:3][CH2:4][CH:5]2[CH2:6][N:7]([C:9]3[N:44]=[C:45]([NH2:46])[N:40]4[N:39]=[C:38]([C:34]5[O:33][CH:37]=[CH:36][CH:35]=5)[N:51]=[C:41]4[N:42]=3)[CH2:8][CH:1]12

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 748322,6-Dichlorobenzyl chlorideHCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amineHCID 225622051,1-Dimethylethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Product 1

HCID 9847558HCID 9847558, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 2,7-diazabicyclo[3.3.0]octane-7-carboxylate (0.3 mmol; see U.S. Pat. No. 5,071,999) dissolved in 2 mL of CH3CN along with 0.3 mmol of 2,6-dichlorobenzyl chloride and 0.5 mmol of Et3N. The reaction mixture was stirred at room temperature for 18 hours. It was then diluted with EtOAc, washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was dissolved in 2 mL of 25% TFA in CH2Cl2 and allowed to stand at room temperature for 3 hours. It was then concentrated to dryness. The resulting residue was dissolved in 3 mL of CH3CN along with 0.3 mmol of 2-furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (see J. Chem. Soc. Perkin Trans. 1, 801 (1995)) and 0.8 mmol of Et3N. The reaction mixture was stirred at reflux for 3 hours. It was then concentrated and purified by preparative HPLC to afford the title compound. 1H NMR (400 Hz, DMSO-d6) δ 8.20 (brs, 1H), 7.8 (d, J=1.0 Hz, 1H), 7.30 (d, J=3.6 Hz, 1H), 7.1-7.30 (m, 3H) 6.60 (dd, J=3.6, 1.0 Hz, 1H), 4.80 (brs, 2H), 2.30-3.8 (m, 10H). MS m/z: 472 [M+H]+.

Workup

  1. washwashed with brine
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in 2 mL of 25% TFA in CH2Cl2
  5. waitto stand at room temperature for 3 hours
  6. concentrationIt was then concentrated to dryness
  7. stirringThe reaction mixture was stirred
  8. temperatureat reflux for 3 hours
  9. concentrationIt was then concentrated
  10. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b7f593ff08a94cd888beb01ca59d7386
Source dataset
uspto-grants-2010_11
Patent number
US07834014B2

Reaction notes

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