2-Nitrophenyl isocyanate → HCID 66641088, compound

HRID 1615968Notes

Reaction equation

HRID 1615968 reaction equation
[NH2:1][CH:2]([CH2:10][NH:11][C:12]1[C:17]([CH2:18][CH3:19])=[C:16]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:35]=[CH:34][C:33]4[CH2:32][CH2:31][CH2:30][NH:29][C:28]=4[N:27]=3)[CH2:22][CH2:21]2)[N:15]=[CH:14][N:13]=1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[N+:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N:45]=[C:46]=[O:47])([O-:38])=[O:37]>O1CCCC1>[CH2:18]([C:17]1[C:12]([NH:11][CH2:10][CH:2]([NH:1][C:46]([NH:45][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N+:36]([O-:38])=[O:37])=[O:47])[C:3]([O:5][C:6]([CH3:8])([CH3:7])[CH3:9])=[O:4])=[N:13][CH:14]=[N:15][C:16]=1[N:20]1[CH2:21][CH2:22][CH:23]([C:26]2[CH:35]=[CH:34][C:33]3[CH2:32][CH2:31][CH2:30][NH:29][C:28]=3[N:27]=2)[CH2:24][CH2:25]1)[CH3:19]

Participants

4

Reactant 2

HCID 768342-Nitrophenyl isocyanateHCID 66641143Tert-butyl 2-amino-3-{5-ethyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionate

Product 1

HCID 66641088HCID 66641088, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 240 mg (0.50 mmole) of tert-butyl 2-amino-3-{5-ethyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionate and 82 mg (0.50 mmole) of 2-nitrophenylisocynate in 15 ml of tetrahydrofuran is stirred for 3 hours at ambient temperature. The reaction mixture is evaporated to dryness under reduced pressure (2 kPa) and the residue is taken up in ethyl acetate and water. The organic phase is separated, dried over magnesium sulphate and the solvent evaporated off under reduced pressure (2 kPa). The residue is chromatographed on alumina eluting with a gradient of ethyl acetate-methylene chloride-methanol from 50-50-0 to 50-50-10. 260 mg of expected product is obtained in the form of a yellow solid.

Workup

  1. customThe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent evaporated off under reduced pressure (2 kPa)
  5. customThe residue is chromatographed on alumina eluting with a gradient of ethyl acetate-methylene chloride-methanol from 50-50-0 to 50-50-10

Sources & evidence

ORD record
ord-a8121a69930843b69649ba668d176102
Source dataset
uspto-grants-2014_07
Patent number
US08765766B2

Reaction notes

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