Potassium Iodide → HCID 24965444, compound

HRID 1161868Notes

Reaction equation

[N:1]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][CH3:26])[CH:19]=2)[N:12]([CH2:27][C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])[C:11]3=[O:34])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:36][CH2:37][OH:38].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[N:12]([CH2:27][C:28]([NH:30][CH:31]([CH3:32])[CH3:33])=[O:29])[C:11](=[O:34])[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([N:1]4[CH2:7][CH2:6][CH2:5][N:4]([CH2:36][CH2:37][OH:38])[CH2:3][CH2:2]4)[CH:9]=3)[N:14]=2)=[CH:19][C:20]=1[O:25][CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

2-(6-(1,4-Diazepan-1-yl)-2-(4-fluoro-3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl)-N-isopropylacetamide (EXAMPLE 1i) (28 mg, 0.06 mmol), 2-bromoethanol (30 mg, 0.017 mL, 0.24 mmol), potassium carbonate (17 mg, 0.12 mmol,) and potassium iodide (1 mg, 5.99 μmol) were combined in a microwave vial and DMF (1 mL) added. The reaction mixture was heated at 100° C. for 5 min in the microwave. LCMS indicated that the desired product was being formed. Additional 2-bromoethanol (30 mg, 0.017 mL, 0.24 mmol) was added and reaction mixture was heated at 100° C. for a further 5 min in the microwave. Product was purified by preparative LCMS to afford 2-{2-(4-fluoro-3-methoxyphenyl)-6-[4-(2-hydroxyethyl)perhydro-1,4-diazepin-1-yl]-4-oxo-4H-quinazolin-3-yl}-N-isopropylacetamide (EXAMPLE 4q) (4 mg, 7.82 μmol, 13%).

Workup

additionadded

Sources & evidence

ORD record: ord-0abe2450704b448baa3e243648b8aae3
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820649B2

Reaction notes

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