Triethylamine → HCID 86692087, compound

HRID 1469110Notes

Reaction equation

HRID 1469110 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH:13]1[CH:22]2[CH:17]([CH:18]=[CH:19][CH:20]=[CH:21]2)[C:16](=[O:23])[CH2:15][CH2:14]1.C(N(CC)CC)C.N1C2C(=CC=CC=2)C=NC=1>O1CCOCC1.CC(=O)OCC>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[N:13]1[CH:22]2[CH:17]([CH:18]=[CH:19][CH:20]=[CH:21]2)[C:16](=[O:23])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9210QuinazolineHCID 111738094-Chloro-6-iodoquinazolineHCID 57088589HCID 57088589, compound

Product 1

HCID 86692087HCID 86692087, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

0.75 g of 4-chloro-6-iodoquinazoline, 0.51 g of 2,3,4a,8a-tetrahydro-1H-quinolin-4-one and 0.96 ml of triethylamine in 5 ml of dioxane are heated at 80° C. in a flask until the quinazoline has reacted completely (HPLC check, about 24 hours). The cooled reaction solution is diluted with EA and washed 3 times with water. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 5-100% in 16 min.), giving 0.40 g of 1-(6-iodoquinazolin-4-yl)-2,3,4a,8a-tetrahydro-1H-quinolin-4-one as yellowish solid (yield 40%, content 91%); MS-FAB (M+H+)=402.0; Rf (polar method): 2.20 min.

Workup

  1. customhas reacted completely (HPLC check, about 24 hours)
  2. customThe cooled reaction solution
  3. washwashed 3 times with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. custompurified by means of column chromatography (gradient heptane: EA 5-100% in 16 min.)

Sources & evidence

ORD record
ord-3293087f03c74bfb8cc8fc4a8b45d050
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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