5-Isocyanato-1,3-dioxaindane → HCID 66640745, compound

HRID 1615969Notes

Reaction equation

HRID 1615969 reaction equation
[N:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)=[C:2]=[O:3].[NH2:13][CH:14]([CH2:22][NH:23][C:24]1[C:29]([CH2:30][CH3:31])=[C:28]([N:32]2[CH2:37][CH2:36][CH:35]([C:38]3[CH:47]=[CH:46][C:45]4[CH2:44][CH2:43][CH2:42][NH:41][C:40]=4[N:39]=3)[CH2:34][CH2:33]2)[N:27]=[CH:26][N:25]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>O1CCCC1>[O:8]1[C:7]2[CH:11]=[CH:12][C:4]([NH:1][C:2](=[O:3])[NH:13][CH:14]([CH2:22][NH:23][C:24]3[C:29]([CH2:30][CH3:31])=[C:28]([N:32]4[CH2:33][CH2:34][CH:35]([C:38]5[CH:47]=[CH:46][C:45]6[CH2:44][CH2:43][CH2:42][NH:41][C:40]=6[N:39]=5)[CH2:36][CH2:37]4)[N:27]=[CH:26][N:25]=3)[C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[CH:5][C:6]=2[O:10][CH2:9]1

Participants

4

Reactant 2

HCID 52232135-Isocyanato-1,3-dioxaindaneHCID 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 66640745HCID 66640745, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

34 mg (0.207 mmoles) of 5-isocyanato-benzo[1,3]dioxole in solution in 3 ml of tetrahydrofuran is added to 120 mg (0.207 mmoles) 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 in solution in 5 ml of tetrahydrofuran. The reaction mixture is stirred at ambient temperature for 3 hours and 30 minutes. Then, the solvent is evaporated off under reduced pressure (2 kPa) and the residue is chromatographed on silica gel with the following eluent: 100% ethyl acetate, ethyl acetate-dichloromethane/methanol (95/5) 50-50, ethyl acetate-dichloromethane/methanol (90-10) 50-50 and finishing with ethyl acetate/methanol (95-5). 60 mg of expected product is obtained.

Workup

  1. customThen, the solvent is evaporated off under reduced pressure (2 kPa)
  2. customthe residue is chromatographed on silica gel with the following eluent

Sources & evidence

ORD record
ord-06e8d49462374427b11514c0d73c5502
Source dataset
uspto-grants-2014_07
Patent number
US08765766B2

Reaction notes

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