Ethyl Acetate → HCID 67994825, compound

HRID 2361324Notes

Reaction equation

HRID 2361324 reaction equation
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N:33]4[CH2:41][C:40]5[C:35](=[CH:36][C:37]([Cl:42])=[CH:38][CH:39]=5)[C:34]4=[O:43])[C:28]=2[CH3:44])=[CH:6][N:5]=1)=[CH:15][CH:14]=[C:13]([NH:17]C(=O)OCC[Si](C)(C)C)[CH:12]=3)(=[O:3])[NH2:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.CCOC(C)=O>O1CCCC1>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]3[C:7]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([N:33]5[CH2:41][C:40]6[C:35](=[CH:36][C:37]([Cl:42])=[CH:38][CH:39]=6)[C:34]5=[O:43])[C:28]=4[CH3:44])=[CH:6][N:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:9]=3[NH:10]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 67995327HCID 67995327, compound

Product 1

HCID 67994825HCID 67994825, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a burgundy, homogeneous solution of 2-(trimethylsilyl)ethyl 1-carbamoyl-4-(3-(6-chloro-1-oxoisoindolin-2-yl)-2-methylphenyl)-9H-pyrido[3,4-b]indol-7-ylcarbamate (0.126 g, 0.201 mmol) in tetrahydrofuran (0.2 mL) was added 1M TBAF/THF (0.402 mL, 0.402 mmol). After 4 hr, EtOAc (80 mL) was added, and the layer was washed with water (20 mL) and brine (20 mL), successively. The organic solution was dried over MgSO4 and concentrated in vacuo to give a crude product as a light brown solid, which was used in the subsequent step.

Workup

  1. washthe layer was washed with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-405fe26f1e3a4775adee5f2df4e594ab
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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