4-[4-(4-Chlorophenyl)-4-hydroxy-piperidin-1-yl]1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}1,3,5-triazin-2(1H)-one → 4-[4-(4-Chlorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

HRID 1477701Notes

Reaction equation

HRID 1477701 reaction equation
OC1(C2C=CC=CC=2)CCN(C2N=CN(CC3SC(C(F)(F)F)=CC=3)C(=O)N=2)CC1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2(O)[CH2:43][CH2:42][N:41]([C:44]3[N:49]=[CH:48][N:47]([CH2:50][C:51]4[S:52][C:53]([C:56]([F:59])([F:58])[F:57])=[CH:54][CH:55]=4)[C:46](=[O:60])[N:45]=3)[CH2:40][CH2:39]2)=[CH:34][CH:33]=1>>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH2:43][CH2:42][N:41]([C:44]3[N:49]=[CH:48][N:47]([CH2:50][C:51]4[S:52][C:53]([C:56]([F:57])([F:58])[F:59])=[CH:54][CH:55]=4)[C:46](=[O:60])[N:45]=3)[CH2:40][CH:39]=2)=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 1178393994-[4-(4-Chlorophenyl)-4-hydroxy-piperidin-1-yl]1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}1,3,5-triazin-2(1H)-oneHCID 1178395044-(4-hydroxy-4-phenylpiperidin-1-yl)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

Product 1

HCID 1178401244-[4-(4-Chlorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

Procedure

The synthesis was performed using the mixture (21 mg) of 4-(4-hydroxy-4-phenylpiperidin-1-yl)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one and 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one that were synthesized in Reference Synthesis Example 91 in a similar manner to Synthesis Example 68. The resultant residue was purified by preparative high performance chromatography to obtain the title compound of Synthesis Example 70 (3.0 mg, yield: 16%) and the title compound of Synthesis Example 71 (7.5 mg, yield: 37%).

Workup

  1. customwere synthesized in Reference Synthesis Example 91 in a similar manner to Synthesis Example 68
  2. customThe resultant residue was purified by preparative high performance chromatography
  3. customto obtain

Sources & evidence

ORD record
ord-03e229c3a9a8409299217fc8df7150d6
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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