HCID 118194448, compound → HCID 118194497, compound

HRID 633727Notes

Reaction equation

HRID 633727 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.[S:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26](=[O:29])[CH2:27]Br)=[CH:25][C:20]=2[N:19]=[N:18]1>>[S:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26](=[O:29])[CH2:27][N:12]3[C:4]4=[N:3][C:2]([Cl:1])=[CH:7][C:6](=[O:8])[N:5]4[CH2:9][CH2:10][C@H:11]3[C:13]([F:14])([F:15])[F:16])=[CH:25][C:20]=2[N:19]=[N:18]1

Participants

3

Reactant 2

HCID 118194448HCID 118194448, compoundHCID 136238740(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one

Product 1

HCID 118194497HCID 118194497, compound

Procedure

150 mg (0.59 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 167.25 mg (0.65 mmol) of 1-benzo[1,2,3]thiadiazol-5-yl-2-bromoethanone were used in the reaction. After purification by chromatography on silica gel (eluent: 90/10 DCM/MeOH), 210 mg of (8S)-9-(2-benzo[1,2,3]thiadiazol-5-yl-2-oxoethyl)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one are obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by chromatography on silica gel (eluent: 90/10 DCM/MeOH), 210 mg of (8S)-9-(2-benzo[1,2,3]thiadiazol-5-yl-2-oxoethyl)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one
  2. customare obtained

Sources & evidence

ORD record
ord-1561e2da330545ffbfce177350bef4ed
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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