HCID 69240704, compound → HCID 69241132, compound

HRID 2237597Notes

Reaction equation

HRID 2237597 reaction equation
COC1C=CC(C[NH:8][C:9]2[N:18]=[C:17]([NH:19][C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH:26]C(=O)OC(C)(C)C)[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:34])[CH:15]=3)[N:10]=2)=CC=1>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:26][C@@H:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]1[NH:19][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:34])[CH:15]=2)[N:10]=[C:9]([NH2:8])[N:18]=1

Participants

4

Reactant 1

HCID 69240704HCID 69240704, compound

Product 1

HCID 69241132HCID 69241132, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 9.37 g of tert-butyl (1R,2S)-2-({2-[(4-methoxybenzyl)amino]-6-methylquinazolin-4-yl}amino)cyclohexylcarbamate in 30 ml of methylene chloride, 95 ml of trifluoroacetic acid was added under ice cooling, and then the mixture was stirred for 72 hours. The reaction solution was concentrated, neutralized with a saturated sodium hydrogencarbonate solution, extracted with chloroform:methanol=10:1 and then dried. The solvent was distilled off and the residue was purified by Fuji Silysia NH silica gel column chromatography (chloroform:methanol=50:1) to obtain 4.60 g of the desirable compound.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with chloroform
  3. dry with materialmethanol=10:1 and then dried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by Fuji Silysia NH silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-c457cd6f1c0948ddb9843e388257c8ab
Source dataset
uspto-grants-2010_05
Patent number
US07718663B2

Reaction notes

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