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

HRID 1499208Notes

Reaction equation

HRID 1499208 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH2:33][CH2:32][C:12]3([CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:13]3)[CH2:11][CH2:10]2)[N:3]=1.[CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][C:35]=1[CH2:44][NH2:45].CCN(CC)CC>C(O)(C)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:45][CH2:44][C:35]2[CH:36]=[CH:37][C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:34]=2)[N:5]=[C:4]([N:9]2[CH2:33][CH2:32][C:12]3([CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:13]3)[CH2:11][CH2:10]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1372821-(2-Naphthyl)methanamineHCID 1179478002-Benzyl 3-ethyl 8-(4-amino-6-chloro-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate

Product 1

HCID 1179427132-Benzyl 3-ethyl 8-(4-amino-6-((naphthalen-2-ylmethyl)amino)-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 2-benzyl 3-ethyl 8-(4-amino-6-chloro-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (265 mg, 0.56 mmol) in isopropanol (3 mL) were added naphthalen-2-ylmethanamine (105 mg, 0.67 mmol) and Et3N (1.4 mL). The reaction mixture was heated to reflux for 12 h, then cooled to RT, and concentrated in vacuo. Purification by normal phase chromatography (CH2Cl2/MeOH) provided 2-benzyl 3-ethyl 8-(4-amino-6-((naphthalen-2-ylmethyl)amino)-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. concentrationconcentrated in vacuo
  4. customPurification by normal phase chromatography (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-f4c9d0b2ff09458988c28a9901b4e817
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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