Triethylamine → HCID 136350273, compound

HRID 77399Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12].Cl.[N:14]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[NH:17][CH2:16][CH2:15]2.C(N(CC)CC)C.CC(C)([O-])C.[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCCC1>[N:14]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[N:17]([C:2]1[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]3=[O:12])[CH2:16][CH2:15]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-bromoquinazolin-4(3H)-one (0.50 g, 2.22 mmol), 1,4-diazabicyclo[3.2.2]nonane hydrochloride (0.44 g, 2.22 mmol), triethylamine (0.45 g, 4.44 mmol), potassium tert-butoxide (0.25 g, 2.22 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (1.06 g, 2.22 mmol) and tris(dibenzyllideneacetone)dipalladium (0) (0.41 g, 0.44 mmol) in Tetrahydrofuran (15 mL) was heated in the microwave at 120° C. for 30 mins. The solvent was evaporated off and to the residue was added methanol and the mixture acidified with acetic acid then loaded on to a 5 g SCX column. The mixture was purified on silica (25 g SNAP column on SP4) eluting with dichloromethane to 60/40 dichloromethane/(2M ammonia in methanol) to afford 6-(1,4-diazabicyclo[3.2.2]nonan-4-yl)quinazolin-4(3H)-one (18.5 mg, 0.07 mmol).

Workup

customThe solvent was evaporated off and to the residue
additionwas added methanol
customThe mixture was purified on silica (25 g SNAP column on SP4)
washeluting with dichloromethane to 60/40 dichloromethane/(2M ammonia in methanol)

Sources & evidence

ORD record: ord-e96f2a10199641c784b47eba6de13383
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841289B2

Reaction notes

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