Diisopropylethylamine → HCID 58459116, compound

HRID 2036632Notes

Reaction equation

HRID 2036632 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]2[CH:18]([NH2:20])[CH3:19])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl[C:22]1[C:27]([C:28]#[N:29])=[CH:26][N:25]=[CH:24][N:23]=1.CC[N:32](C(C)C)C(C)C>C(O)CCC.CCOC(C)=O>[NH2:32][C:22]1[C:27]([C:28]#[N:29])=[C:26]([NH:20][CH:18]([C:10]2[N:9]([C:4]3[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=3)[C:17]3[C:12]([N:11]=2)=[N:13][CH:14]=[CH:15][CH:16]=3)[CH3:19])[N:25]=[CH:24][N:23]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 131269094-Chloropyrimidine-5-carbonitrileHCID 58459169HCID 58459169, compound

Product 1

HCID 58459116HCID 58459116, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-[1-(3,5-difluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]-ethylamine (200 mg, 0.729 mmol) and 4-chloro-pyrimidine 5-carbonitrile (112 mg, 0.729 mmol) in n-butanol (2.18 mL) was added DIEA (282 mg, 2.187 mmol) at rt. The reaction mixture was heated at 120° C. overnight. After completion, the reaction mixture was diluted with EtOAc and the resulting solid was collected by filtration to provide 4-amino-6-{1-[1-(3,5-difluorophenyl)-1H-imidazo[4,5-b]-pyridin-2-yl]ethylamino}-pyrimidine-5-carbonitrile: 1H NMR (400 MHz, DMSO-d6) δ 1.597 (d, J=6.8 Hz, 3H), 5.631-5.698 (m, 1H), 7.201 (br s, 2H), 7.255-7.287 (m, 1H), 7.363-7.409 (m, 3H), 7.663 (d, J=7.6 Hz, 1H), 7.759 (d, J=7.6 Hz, 1H), 7.882 (s, 1H), 8.462 (d, J=3.6 Hz, 1H); LC-MS (ESI) m/z 393.1 [M+H]+.

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-d10d6bf9c37b42b49dca1d08cf29f4fa
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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