Triethylamine → 2-Benzyl 3-ethyl 8-(4-amino-6-chloro-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate

HRID 1499207Notes

Reaction equation

HRID 1499207 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH2:9])[N:3]=1.[CH2:10]1[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:13][CH:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].CCN(CC)CC>C(O)(C)C>[NH2:9][C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([N:17]2[CH2:16][CH2:15][C:14]3([CH2:10][N:11]([C:25]([O:27][CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[O:26])[CH:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13]3)[CH2:19][CH2:18]2)[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 136154,6-Dichloro-1,3,5-trazin-2-amineHCID 1179417662-Benzyl 3-ethyl 2,8-diazaspiro[4.5]decane-2,3-dicarboxylate

Product 1

HCID 1179478002-Benzyl 3-ethyl 8-(4-amino-6-chloro-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-1,3,5-triazin-2-amine (1.6 g) in isopropanol (14 mL) was added 2-benzyl 3-ethyl 2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (1.28 g, 3.7 mmol) and Et3N (7 mL). The solution was heated to reflux for 72 h, then cooled to RT, and concentrated in vacuo. Purification by normal phase chromatography (CH2Cl2/MeOH=50/1) afforded 2-benzyl 3-ethyl 8-(4-amino-6-chloro-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate as a colorless oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 72 h
  3. concentrationconcentrated in vacuo
  4. customPurification by normal phase chromatography (CH2Cl2/MeOH=50/1)

Sources & evidence

ORD record
ord-933713ffad524489a366d0d2ab4a6ff3
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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