Diisopropylethylamine → 6-(4-(1-(2-(azetidin-1-yl)ethyl)-4-(2-(trifluoromethyl)pyridin-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)-5-bromopyrimidin-4-amine

HRID 2284046Notes

Reaction equation

HRID 2284046 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.Cl.[N:11]1([CH2:15][CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[N:19]=[C:18]2[CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH2:14][CH2:13][CH2:12]1.C(N(C(C)C)C(C)C)C>C(#N)C>[N:11]1([CH2:15][CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=3)[N:19]=[C:18]2[CH:32]2[CH2:33][CH2:34][N:35]([C:7]3[N:6]=[CH:5][N:4]=[C:3]([NH2:9])[C:2]=3[Br:1])[CH2:36][CH2:37]2)[CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 89442760HCID 89442760, compound

Product 1

HCID 894427596-(4-(1-(2-(azetidin-1-yl)ethyl)-4-(2-(trifluoromethyl)pyridin-4-yl)-1H-imidazol-2-yl)piperidin-1-yl)-5-bromopyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A reaction mixture of 5-Bromo-6-chloro-pyrimidin-4-ylamine (53.00 mg; 0.25 mmol; 1.00 eq.), 4-[1-(2-azetidin-1-yl-ethyl)-2-piperidin-4-yl-1H-imidazol-4-yl]-2-trifluoromethyl-pyridine hydrochloride (4) (133.56 mg; 0.25 mmol; 1.00 eq.), and ethyl-diisopropyl-amine (0.23 ml; 1.27 mmol; 5.00 eq.) in ACN 3 ml was stirred at 80° C. for overnight. Purified by HPLC (basic), collected title compound, 30 mg, yield, 21%. LC-MS: (M+1=551, obsd.=551).

Workup

  1. customPurified by HPLC (basic)
  2. customcollected title compound, 30 mg
  3. customyield

Sources & evidence

ORD record
ord-4b4b96beeaae48569a5b396b837cb59d
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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