1-Tert-butylpiperazine → HCID 66558242, compound

HRID 1530491Notes

Reaction equation

HRID 1530491 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH:23]=O)=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].[C:25]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([CH3:28])([CH3:27])[CH3:26].[BH3-]C#N.[Na+]>CCO>[C:25]([N:29]1[CH2:34][CH2:33][N:32]([CH2:23][C:14]2[CH:15]=[CH:16][C:17]3[O:18][CH2:19][CH2:20][N:21]4[CH:22]=[C:9]([C:8]5[N:4]([CH:2]([CH3:1])[CH3:3])[N:5]=[CH:6][N:7]=5)[N:10]=[C:11]4[C:12]=3[CH:13]=2)[CH2:31][CH2:30]1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 35305721-Tert-butylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 86671457HCID 86671457, compound

Product 1

HCID 66558242HCID 66558242, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-13-carbaldehyde (50 mg, 0.16 mmol) in EtOH (5.0 mL) was added 1-tert-butylpiperazine (46 mg, 0.32 mmol) and Ti(Oi-Pr)4 (88 mg, 0.31 mmol). The mixture was stirred at room temperature for 30 min. NaBH3CN (20 mg, 0.32 mmol) was added and the reaction mixture was further stirred at room temperature for overnight. The solid was filtered, and the filtrate was concentrated and purified by reverse phase combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to give 108 (16 mg, 25% yield). LCMS (ESI): RT=4.92 min, m/z: 450.4 [M+H+]. 1H NMR (500 MHz, CD3OD): δ 8.41 (d, J=2 Hz, 1H), 7.92 (d, J=3 Hz, 1H), 7.20 (dd, J=8.5 Hz, 2.5 Hz, 1H), 7.00 (d, J=8.5 Hz, 1H), 5.90-5.85 (m, 1H), 4.43-4.51 (m, 4H), 3.47 (s, 2H), 2.51-2.39 (m, 8H), 1.51-1.46 (m, 6H), 0.98 (s, 9H)

Workup

  1. stirringthe reaction mixture was further stirred at room temperature for overnight
  2. filtrationThe solid was filtered
  3. concentrationthe filtrate was concentrated
  4. custompurified by reverse phase combiflash
  5. washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-b93d45ebca8a4934825c63b824a6e8fd
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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