(-)-1-Cyclohexylethylamine → HCID 58588514, compound

HRID 1361668Notes

Reaction equation

HRID 1361668 reaction equation
Cl.[F:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][CH3:26])[N:20]=3)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH:27]1([C@H:33]([NH2:35])[CH3:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C1COCC1>[CH:27]1([C@H:33]([NH:35][C:5](=[O:6])[C:4]2[CH:8]=[C:9]([O:12][C:13]3[C:18]([C:19]4[CH:24]=[CH:23][N:22]=[C:21]([NH:25][CH3:26])[N:20]=4)=[CH:17][CH:16]=[CH:15][N:14]=3)[CH:10]=[CH:11][C:3]=2[F:2])[CH3:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 10997046(-)-1-CyclohexylethylamineHCID 86602593HCID 86602593, compound

Product 1

HCID 58588514HCID 58588514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-5-[3-(2-methylamino-pyrimidin-4-yl)-pyridin-2-yloxy]-benzoyl chloride hydrochloride (86 mg, 0.22 mmol) in THF (2.0 mL) was added (R)-1-cyclohexyl-ethylamine (0.029 mL, 0.20 mmol). The mixture was stirred overnight at RT, quenched with excess NEt3, concentrated and purified by preparative TLC (100% EtOAc) to yield N-((1R)-1-cyclohexylethyl)-2-fluoro-5-((3-(2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)benzamide. MS m/z=450 [M+1]+. Calc'd for C25H28FN5O2: 449.53.

Workup

  1. customquenched with excess NEt3
  2. concentrationconcentrated
  3. custompurified by preparative TLC (100% EtOAc)

Sources & evidence

ORD record
ord-6d9aa9d5c7924d5b830e4bf3dbe162cd
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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