Triethylamine → HCID 9932869, compound

HRID 1271877Notes

Reaction equation

HRID 1271877 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([C:34](=[O:37])[CH:35]=[CH2:36])[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(Cl)(=O)C=C.C(OC(=O)NCCNC(C1N(CC2C=CC=CC=2)C(=O)C2C(=CC(Cl)=CC=2)N=1)C(C)C)(C)(C)C.CCN(CC)CC>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:34](=[O:37])[CH2:35][CH2:36][NH:7][CH2:8][CH2:9]1)[CH:12]([CH3:13])[CH3:14])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 18455022HCID 18455022, compoundHCID 69475385HCID 69475385, compound

Product 1

HCID 9932869HCID 9932869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2-{Acryloyl-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-amino}-ethyl)-carbamic acid tert-butyl ester: Acryloyl chloride (126 μL, 1.6 mmol) was added to {2-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-ethyl}-carbamic acid tert-butyl ester (500 mg, 1.03 mmol) and Et3N (216 μL, 0.15 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (10 mL), washed with brine, dried and concentrated under vacuum. Purification by flash chromatography on silica gel (10% EtOAc/hexane) gave the title compound (310 mg) as a white solid: MS (ES) m/e 539.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-f497c78dee284906b18ff89b6f226638
Source dataset
uspto-grants-2007_04
Patent number
US07208487B2

Reaction notes

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