Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine

HRID 1352774

Reaction equation

HRID 1352774 reaction equation
C(S([C:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([N:20]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]2)[N:13]=[C:12]([N:27]2[CH2:32][CH2:31][N:30]3[CH:33]=[CH:34][N:35]=[C:29]3[CH2:28]2)[N:11]=1)=O)C1C=CC=CC=1.[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40][NH2:41].C(N(CC)CC)C>CN(C)C(=O)C>[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40][NH:41][C:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([N:20]2[CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][CH2:25]2)[N:13]=[C:12]([N:27]2[CH2:32][CH2:31][N:30]3[CH:33]=[CH:34][N:35]=[C:29]3[CH2:28]2)[N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 178483354-Benzylsulfinyl-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine

Product 1

HCID 178483124-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-benzylsulfinyl-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine (prepared in the above (6)) 83 mg, 3-chloro-4-methoxybenzylamine 86 mg, triethylamine 51 mg and N,N-dimethylacetoamide 3 ml is stirred at 110° C. for 1 hour. The reaction mixture is diluted with ice water and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; ethyl acetate→ethyl acetate:methanol=15:1→10:1) and crystallized from a mixture of methanol, ethyl acetate and isopropyl ether to give 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine as a colorless crystalline powder 43 mg. mp 192–194° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is separated with silica gel chromatography (solvent; ethyl acetate→ethyl acetate:methanol=15:1→10:1)
  6. customcrystallized from a mixture of methanol, ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-e4d4b0e791ed4b8786366fd29d90e4d3
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Linked notes

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