Triethylamine → HCID 178482382, compound

HRID 2403266Notes

Reaction equation

HRID 2403266 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:7]=[C:6]([NH:17][CH3:18])[N:5]=1.[C:19]([O:23][C:24](=[O:35])[NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([CH2:32][CH:33]=O)[CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[C:19]([O:23][C:24](=[O:35])[NH:25][C@H:26]1[CH2:27][CH2:28][C@H:29]([CH2:32][CH2:33][N:14]2[CH2:15][CH2:16][N:11]([C:8]3[C:9]([Cl:10])=[C:4]([Cl:3])[N:5]=[C:6]([NH:17][CH3:18])[N:7]=3)[CH2:12][CH2:13]2)[CH2:30][CH2:31]1)([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57443709HCID 57443709, compoundHCID 178453924HCID 178453924, compound

Product 1

HCID 178482382HCID 178482382, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5.36 g (16 mmol) of (4,5-dichloro-6-piperazin-1-yl-pyrimidin-2-yl)-methyl-amine dihydrochloride and 3.86 g (16 mmol) of trans-4-(2-oxoethyl)cyclohexyl-carbamic acid tert-butyl ester were dissolved in dichloromethane (320 ml). 6.7 ml (48 mmol) triethylamine was added, then 5.1 g (24 mmol) sodium triacetoxyborohydride was added portion wise and the reaction mixture was stirred for 20 hours at ambient temperature. 20% potassium carbonate solution in water (100 ml) was then added. The organic layer was separated, dried and evaporated to dryness in vacuo. The residue was triturated with diethyl ether to give the title compound (6.9 g, 88.5%), melting point: 199-202° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated to dryness in vacuo
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-1f21928890ce45edbeb055a20e83fd35
Source dataset
uspto-grants-2014_08
Patent number
US08802672B2

Reaction notes

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