Dichloromethane → HCID 71284112, compound

HRID 1481808Notes

Reaction equation

HRID 1481808 reaction equation
C([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[C:32]3[C:28]([C:29]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][C:30]=4[NH:31]3)=[CH:27][CH:26]=2)[C:22]([CH2:39][CH3:40])=[C:21]([O:41]CC2C=CC=CC=2)[C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.C(Cl)Cl.[SiH](C(C)C)(C(C)C)C(C)C>C(O)(C(F)(F)F)=O>[CH2:39]([C:22]1[C:21]([OH:41])=[C:10]([C:11]([OH:13])=[O:12])[C:9](=[O:8])[NH:24][C:23]=1[C:25]1[CH:33]=[C:32]2[C:28]([C:29]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][C:30]=3[NH:31]2)=[CH:27][CH:26]=1)[CH3:40]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 138754Silane, tris(1-methylethyl)-HCID 71285006HCID 71285006, compound

Product 1

HCID 71284112HCID 71284112, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The intermediate from Step 2 (19 mg, 0.030 mmol) was stirred in TFA (0.2 mL), CH2Cl2 (0.2 mL) and TIPSH (0.2 mL) at room temperature for 15 h. The solvents were removed and the residue was dissolved in CH2Cl2 (0.5 mL), then HCl (2.0M in Et2O, 1.0 mL) was added. The precipitate was collected by filtration and washed by ether to afford the title compound as an off-white solid (12 mg, 0.030 mmol, HCl salt) in 100% yield.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in CH2Cl2 (0.5 mL)
  3. additionHCl (2.0M in Et2O, 1.0 mL) was added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed by ether

Sources & evidence

ORD record
ord-821cf0c9cad5424eb4cdbbee182036d5
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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