Ethanol → HCID 86685007, compound

HRID 1518984Notes

Reaction equation

HRID 1518984 reaction equation
[CH2:1]([O:10][C:11]1[N:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:20]N.[CH3:22][CH2:23]O>C(Cl)Cl>[NH2:20][CH2:23][CH2:22][C:15]1[NH:16][C:17]2[C:13]([CH:14]=1)=[N:12][C:11]([O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:19][CH:18]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 86685008HCID 86685008, compound

Product 1

HCID 86685007HCID 86685007, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

N-phthaloyl protected 5-nonyloxy-4-azaindole (20 mg, 0.05 mmole) and hydrazine (3 mg, 0.09 mmole) was dissolved in CH2Cl2 (0.5 mL) in a 25 mL round bottom flask. EtOH (1 mL) was added to the reaction mixture and allowed to stir overnight at 25° C. for 12 h, after which it was cooled to 0° C., and filtered, and the white solid material was washed with 3 mL of cold CH2Cl2. The filtrate was evaporated under reduced pressure to afford 7 mg (50%) of 2-aminoethyl-5-nonyloxy-4-azaindole as a yellow solid. LRMS (ESI): M+1 for C18H29N3O calcd 304.4. found 304.4.

Workup

  1. temperatureafter which it was cooled to 0° C.
  2. filtrationfiltered
  3. washthe white solid material was washed with 3 mL of cold CH2Cl2
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-152469a419f54f7e9dcbf9cc3ad278b4
Source dataset
uspto-grants-2015_07
Patent number
US09073851B2

Reaction notes

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