tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamate → HCID 67539006, compound

HRID 1192331Notes

Reaction equation

HRID 1192331 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([C:18](Cl)=[O:19])[CH2:14][CH2:13]2)=[N:4][CH:3]=1.[C:21]([O:25][C:26](=[O:39])[NH:27][CH2:28][CH2:29][NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:21]([O:25][C:26](=[O:39])[NH:27][CH2:28][CH2:29][N:30]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:18]([CH:15]1[CH2:16][CH2:17][N:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:2]=[CH:3][N:4]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 67134877tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamateHCID 86598731HCID 86598731, compound

Product 1

HCID 67539006HCID 67539006, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Step 1-Quinazolin-4-yl-piperidine-4-carbonyl chloride hydrochloride (197 mg, 0.63 mmol) was added to a solution of [2-(4-chlorobenzylamino)-ethyl]-carbamic acid tert-butyl ester (180 mg, 0.63 mmol) and DMAP (154 mg, 1.26 mmol) in DCM (6.5 mL) cooled in an ice bath. After being stirred for 12 hours, the mixture was partitioned between DCM (50 mL) and H2O (80 mL) containing 1 mL of 1.0 M HCl. The DCM layer was drained off and the acidic aqueous layer was extracted 3 more times with DCM. The combined DCM extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2) using EtOAc as eluent to give {2-[(4-chlorobenzyl)-(1-quinazolin-4-yl-piperidine-4-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester (190 mg).

Workup

  1. temperaturecooled in an ice bath
  2. customthe mixture was partitioned between DCM (50 mL) and H2O (80 mL)
  3. additioncontaining 1 mL of 1.0 M HCl
  4. extractionthe acidic aqueous layer was extracted 3 more times with DCM
  5. dry with materialThe combined DCM extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was chromatographed (SiO2)

Sources & evidence

ORD record
ord-db975a51995841c6bc863dc49fec8316
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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