Disodium disulfite → HCID 136236986, compound

HRID 1050960Notes

Reaction equation

HRID 1050960 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].O1CCO[CH:13]1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>CN(C)C(=O)C>[F:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:13]([C:17]1[CH:18]=[CH:19][C:20]([C:23]3([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:21][CH:22]=1)[NH:6][C:4]2=[O:5]

Participants

5

Reactant 3

HCID 24346Disodium disulfiteHCID 102410032-Amino-5-fluorobenzamideHCID 118272349HCID 118272349, compound

Product 1

HCID 136236986HCID 136236986, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 2-amino-5-fluorobenzamide (135 mg, 0.88 mmol), 1-(4-[1,3]dioxolan-2-yl-phenyl)-cyclopentanol (206 mg, 0.88 mmol) and sodium disulfite (170 mg, 0.89 mmol) in N,N-dimethylacetamide (2 ml) is heated to 150° C. and stirred at this temperature for 3 hours. The reaction mixture is allowed to reach room temperature and poured into ice water. The resulting precipitate is collected by filtration and washed with water. It is chromatographed on a silica gel column with methanol/dichloromethane as eluent to afford 6-fluoro-2-[4-(1-hydroxy-cyclopentyl)-phenyl]-3H-quinazolin-4-one as white solid; HPLC/MS 1.80 min (A), [M+H] 325;

Workup

  1. customto reach room temperature
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with water
  4. customIt is chromatographed on a silica gel column with methanol/dichloromethane as eluent

Sources & evidence

ORD record
ord-364b86a8df2e405b91196eea50074bc8
Source dataset
uspto-grants-2016_07
Patent number
US09388142B2

Reaction notes

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