Water → HCID 59849192, compound

HRID 604278Notes

Reaction equation

HRID 604278 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([OH:28])=[O:27])[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[CH2:8][CH2:7]2.[Cl:29][C:30]1[N:35]=[C:34](Cl)[C:33]([Cl:37])=[CH:32][N:31]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[C:6]([O:27][C:26]([N:23]1[CH2:22][CH2:21][N:20]([CH:17]2[CH2:18][CH2:19][N:14]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:32]4[C:33]([Cl:37])=[CH:34][N:35]=[C:30]([Cl:29])[N:31]=4)=[C:11]4[C:6]=3[CH2:7][CH2:8][N:9]([CH3:13])[C:10]4=[O:12])[CH2:15][CH2:16]2)[CH2:25][CH2:24]1)=[O:28])([CH3:11])([CH3:7])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 67038070HCID 67038070, compound

Product 1

HCID 59849192HCID 59849192, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture 4-[1-(8-amino-2-methyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-piperidin-4-yl]-piperazine-1-carboxylic acid #tert!-butyl ester (9.20 g, 20.7 mmol), 2,4,5-trichloropyrimidine (5.96 mL, 51.8 mmol), K2CO3 (7.17 g, 51.8 mmol) in DMSO (200 mL) was stirred at 60° C. for 12 hours. After cooling to room temperature, 700 mL of water was added with stirring. The mixture was filtrated. The resulting brown solids were suspended in CH3CN (ca. 200 mL), stirred for a while and filtrated. The residue was further washed with CH3CN and dried under reduced pressure to give 8.75 g of 4-{1-[8-(2,5-dichloro-pyrimidin-4-ylamino)-2-methyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl]-piperidin-4-yl}-piperazine-1-carboxylic acid tert-butyl ester as pale beige solids in 72% yield.

Workup

  1. filtrationThe mixture was filtrated
  2. stirringstirred for a while
  3. filtrationfiltrated
  4. washThe residue was further washed with CH3CN
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3f681178ded1478294180f25ccb605da
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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