1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178521595, compound

HRID 1672458Notes

Reaction equation

HRID 1672458 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1.C1CCN2C(=NCCC2)CC1>CC#N>[O:16]1[CH2:17][CH2:18][CH:13]([O:12][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([NH:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]2)[N:11]=[CH:10]3)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58082185HCID 58082185, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178521595HCID 178521595, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-chloro-8-(tetrahydro-2H-pyran-4-yloxy)quinazoline (1 g, 3.8 mmol), trans-4-amino-cyclohexanol (0.524 g, 4.56 mmol) and DBU (0.69 g, 4.56 mmol) were suspended in MeCN (10 mL). The mixture was heated at reflux for 10 h. TLC showed the reaction was complete. The mixture was concentrated in vacuo, the residue was purified by HPLC to yield the title compound (0.373 g, 28%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 10.817 (d, 1H), 9.120 (s, 1H), 7.351 (m, 2H), 7.210 (m, 1H), 4.630 (m, 1H), 4.118 (m, 1H), 4.041 (m, 2H), 3.712 (m, 1H), 3.524 (m, 2H), 2.001 (m, 8H), 1.620 (q, 2H), 1.419 (q, 2H)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-741aff5dc67641e8911676565f03bda9
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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