Ammonia → HCID 117988239, compound

HRID 63799Notes

Reaction equation

HRID 63799 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:16]3=[CH:25][C:26]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:27][N:15]3[N:14]=2)[CH:8]=1)(=O)=O.[NH3:32]>CO>[NH2:32][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:16]3=[CH:25][C:26]([CH2:28][N:29]([CH3:30])[CH3:31])=[CH:27][N:15]3[N:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 117988030HCID 117988030, compound

Product 1

HCID 117988239HCID 117988239, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 19 (80 mg, 0.18 mmol) was added to 20 mL of saturated ammonia solution of methanol. The reaction was carried out at 80° C. in a sealed tube for 8 h. After the reaction mixture was concentrated, it was purified by a preparative plate (dichloromethane:methanol=6:1) to obtain 37 mg of colourless oil (56.2%). 1H NMR (300 MHz, CDCl3): δ 8.20 (s, 1H), 8.17-8.13 (m, 1H), 7.64 (s, 1H), 7.41-7.39 (m, 2H), 6.86 (s, 1H), 4.11 (t, J=4.7 Hz, 4H), 3.97 (s, 2H), 3.87 (t, J=4.7 Hz, 4H), 3.69 (s, 2H), 2.41 (s, 6H). LC-MS: 367 (M+1).

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. customit was purified by a preparative plate (dichloromethane:methanol=6:1)

Sources & evidence

ORD record
ord-eacff03b882544d9898b5c146746d21c
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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