Dabco → HCID 59655715, compound

HRID 2054422Notes

Reaction equation

HRID 2054422 reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].N12CCN(CC1)CC2.C(N(C(C)C)CC)(C)C.Cl[C:28]1[N:33]2[N:34]=[C:35]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[Cl:50])[C:36]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)=[C:32]2[N:31]=[C:30]([CH3:51])[N:29]=1>O1CCCC1>[C:1]([N:5]1[CH2:8][CH:7]([O:9][C:28]2[N:33]3[N:34]=[C:35]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[Cl:50])[C:36]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)=[C:32]3[N:31]=[C:30]([CH3:51])[N:29]=2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 9237DabcoHCID 81531DiisopropylethylamineHCID 2879861-tert-Butyl-3-hydroxyazetidineHCID 59655729HCID 59655729, compound

Product 1

HCID 59655715HCID 59655715, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butylazetidin-3-ol (19 mg, 0.15 mmol), 1,4-diazabicyclo[2.2.2]octane (11 mg, 0.10 mmol), and diisopropylethylamine (0.026 ml, 0.15 mmol) in tetrahydrofuran (1 ml) was added 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 39 mg, 0.10 mmol), portionwise. After stirring for 2 days, the reaction was concentrated, in vacuo, and the residue purified on a Biotage™ Flash 12S column using 20-40% ethyl acetate in hexanes to afford 11A-1 (25 mg, 52%) as a solid: +APcI MS (M+1) 482.3; 1H NMR (400 MHz, CD3OD) δ 7.52-7.42 (m, 4H), 7.39 (d, J=8.3 Hz, 2H), 7.24 (d, J=8.3 Hz, 2H), 5.58 (quintet, J=6.2 Hz, 1H), 3.80-3.75 (m, 2H), 3.63-3.58 (m, 2H), 2.60 (s, 3H), 1.04 (s, 9H).

Workup

  1. concentrationthe reaction was concentrated, in vacuo
  2. customthe residue purified on a Biotage™ Flash 12S column
  3. customto afford 11A-1 (25 mg, 52%) as a solid

Sources & evidence

ORD record
ord-2f0f535158c64fe5830d189d275ecda4
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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