Dicyclohexylcarbodiimide → HCID 131726734, compound

HRID 556632Notes

Reaction equation

HRID 556632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](NCCN)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].[C:32]([O:36][C:37]([NH:39][CH2:40][C:41]([OH:43])=O)=[O:38])([CH3:35])([CH3:34])[CH3:33].[CH:44]1([N:50]=C=NC2CCCCC2)CCCC[CH2:45]1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][CH2:16][N:17]([C:41](=[O:43])[CH2:40][N:39]([C:37]([O:36][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:38])[CH2:45][CH2:44][NH2:50])[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH:12]=[CH:11][C:10]1=[O:31]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 596395772-[(2-Aminoethyl)amino]-8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 131726734HCID 131726734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound of Example 157 (168 mg, 0.0004 mol) in dry THF (2 mL) with tert-butoxycarbonylglycine (70 mg, 0.0004 mol) was treated with dicyclohexylcarbodiimide (82.4 mg, 0.0004 mol) in dry THF (2 mL). The solution was stirred 16h at 23°; filtered and stripped to dryness. The residue was taken up in methylene chloride (5 mL) and applied to a Chromatotron™ Rotor Plate (1000 u thickness); plate eluted with methylene chloride-methanol gradient (0% to 3% MeOH). This afforded 122 mg (52%) of the title compound as a light red solid. LC MS (m/e)=583(MH+). Rt=2.12 min.

Workup

  1. filtrationfiltered
  2. washplate eluted with methylene chloride-methanol gradient (0% to 3% MeOH)

Sources & evidence

ORD record
ord-aea311c4505445d89fa8905aa83cbfdf
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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