tert-butyl N-(2-oxoethyl)carbamate → HCID 9932869, compound

HRID 1271876Notes

Reaction equation

HRID 1271876 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][NH:10][CH:11]([C:15]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[C:22]2[C:17](=[CH:18][C:19]([Cl:33])=[CH:20][CH:21]=2)[N:16]=1)[CH:12]([CH3:14])[CH3:13])(C)(C)C.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=[O:37])[CH3:36].[Na+].NC(C1N(CC2C=CC=CC=2)C(=O)C2C(=CC(Cl)=CC=2)N=1)C(C)C.O=CCNC(=O)OC(C)(C)C>C(Cl)Cl>[CH2:25]([N:24]1[C:23](=[O:32])[C:22]2[C:17](=[CH:18][C:19]([Cl:33])=[CH:20][CH:21]=2)[N:16]=[C:15]1[CH:11]([N:10]1[C:35](=[O:37])[CH2:36][CH2:6][NH:7][CH2:8][CH2:9]1)[CH:12]([CH3:14])[CH3:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 18455022HCID 18455022, compoundHCID 222387982-(1-amino-2-methylpropyl)-3-benzyl-7-chloroquinazolin-4(3H)-one

Product 1

HCID 9932869HCID 9932869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Preparation of {2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-ethyl}-carbamic acid tert-butyl ester: Sodium triacetoxyborohydride (172 mg, 0.81 mmol) was added to a solution containing 2-(1-amino-2-methyl-propyl)-3-benzyl-7-chloro-3H-quinazolin-4-one (185 mg, 0.54 mmol) (prepared using the general procedure described in WO 0130768) and tert-butyl N-(2-oxoethyl)carbamate (103 mg, 0.65 mmol) in CH2Cl2 (5.4 mL). The resulting mixture was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 (10 mL), washed with brine, dried and concentrated under vacuum. Purification by flash chromatography on silica gel (5–10% EtOAc in hexane) gave the title compound (105 mg) as a white solid: MS (ES) m/e 485 (M+H)+.

Workup

  1. customprepared
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customPurification by flash chromatography on silica gel (5–10% EtOAc in hexane)

Sources & evidence

ORD record
ord-379cbff2e277442fa796ec9369a063c8
Source dataset
uspto-grants-2007_04
Patent number
US07208487B2

Reaction notes

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