HCID 178487824, compound → HCID 178422137, compound

HRID 55781Notes

Reaction equation

HRID 55781 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:21]([CH3:22])=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:23]C)[CH:18]=4)[N:13]=3)=[CH:8][CH:7]=2)=[N:4][N:3]=[N:2]1>CN1C(=O)CCC1>[NH:4]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:21]([CH3:22])=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([OH:23])[CH:18]=4)[N:13]=3)=[CH:8][CH:7]=2)=[N:1][N:2]=[N:3]1

Participants

3

Reactant 1

HCID 178487824HCID 178487824, compound

Product 1

HCID 178422137HCID 178422137, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline (128 mg, 0.40 mmol) was dissolved in 5 mL of NMP and Na2S (47 mg, 0.60 mmol) was added to it. The mixture was then stirred for 4 hours at 140° C. in a microwave reactor. After concentration in vacuo the crude was dissolved in 5 mL of 1N NaOH and slowly acidified with 1N HCl to a pH of 4. The solids were filtered and dried in vacuo to afford 46.2 mg (38% yield) of Compound 2. 1H NMR (DMSO-d6, 400 MHz): δ 10.10-10.00 (bs, 1H), 8.18-8.15 (d, 2H), 8.08 (s, 1H), 7.87-7.84 (m, 3H), 7.30-7.26 (d, 1H), 7.13 (s, 1H), 2.45 (s, 3H). MS (ESI): m/z 304.11 [M+H]+.

Workup

  1. concentrationAfter concentration in vacuo the crude
  2. dissolutionwas dissolved in 5 mL of 1N NaOH
  3. filtrationThe solids were filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-38d7ba10dbea4a1dae25d68ff5ee7f66
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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