Triphenylphosphine → HCID 66875590, compound

HRID 2079788Notes

Reaction equation

HRID 2079788 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18]([C:21]1[N:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][N:22]=1)[CH2:19]2)(=[O:13])=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:52][CH2:53][N:54]1[CH:58]=[CH:57][N:56]=[C:55]1[CH3:59].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH3:59][C:55]1[N:54]([CH2:53][CH2:52][N:14]([S:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:13])=[O:12])[CH:15]2[CH:16]3[CH:20]2[CH2:19][N:18]([C:21]2[N:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][N:22]=2)[CH2:17]3)[CH:58]=[CH:57][N:56]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 741692-Methyl-1H-imidazole-1-ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 59367563HCID 59367563, compound

Product 1

HCID 66875590HCID 66875590, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-[6-(naphthalene-2-sulfonylamino)-3-aza-bicyclo[3.1.0]hex-3-yl]-pyrimidine-5-carboxylate (0.182 g, 0.47 mmol) in DCM (10 ml) was added triphenylphosphine (0.26 g, 1 mmol) and 1-(2-hydroxyethyl)-2-methylimidazole (0.084 mg, 0.75 mmol). Diisopropylazodicarboxylate (0.167 ml, 0.85 mmol) was then added and the solution stirred overnight. The mixture was loaded directly onto a silica gel column and purified eluting with 2% MeOH/DCM to give the title compound (0.242 g, 90%). 1H NMR (300 MHz, CDCl3) δ: 1.36 (3H, t), 1.60-1.80 (3H, m), 2.57 (3H, s), 3.43 (2H, t), 3.48-3.62 (2H, m), 3.70 (2H, d), 4.35 (2H, t), 4.33 (2H, q), 6.90 (1H, d), 6.98 (1H, d), 7.60-7.80 (2H, m) 7.82 (1H, dd), 7.95 (1H, dd), 8.02 (2H, d), 8.43 (1H, s), 8.72 (2H, s).

Workup

  1. custompurified
  2. washeluting with 2% MeOH/DCM

Sources & evidence

ORD record
ord-c5ec72d6181a4eb4a9aadb3792d7b6f7
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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