1-Hydroxybenzotriazole → HCID 67248916, compound

HRID 2175093Notes

Reaction equation

HRID 2175093 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:17]=[CH:16][CH:15]=3)[CH:5]=[CH:4][C:3]1=2.C(OC([NH:34][C@H:35]([C:39](O)=[O:40])[C@@H:36]([CH3:38])[OH:37])=O)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C>C1COCC1>[NH2:34][C@@H:35]([CH:36]([OH:37])[CH3:38])[C:39]([N:23]1[CH2:22][CH2:21][N:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:6]3[CH:5]=[CH:4][C:3]4[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=4[CH:7]=3)[N:19]=2)[CH2:25][CH2:24]1)=[O:40]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 53250560HCID 53250560, compound

Product 1

HCID 67248916HCID 67248916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.57 mmol) of 1-[6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-pyridin-2-yl]piperazine, 138 mg (0.629 mmol) of N-(tert-butoxycarbonyl)-L-threonine, 105 mg (0.69 mmol) of HOBt, 132 mg (0.69 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 291 μl (1.72 mmol) of DIPEA are dissolved in 5 ml of THF and stirred at room temperature for 18 h. The crude product was purified by column chromatography and silica gel, dissolved in dioxane, and an excess of 4N HCl in dioxane was added. The reaction mixture is stirred at room temperature for 12 h, evaporated and purified by means of preparative HPLC. The product is converted into the hydrochloride using methanolic HCl.

Workup

  1. customThe crude product was purified by column chromatography and silica gel
  2. dissolutiondissolved in dioxane
  3. additionan excess of 4N HCl in dioxane was added
  4. stirringThe reaction mixture is stirred at room temperature for 12 h
  5. customevaporated
  6. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-ac85930487a1412ab01d928013ce7a65
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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