Ammonia → HCID 56960208, compound

HRID 1753783Notes

Reaction equation

HRID 1753783 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([C:24]([O:26]CC)=O)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:29]>O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([C:24]([NH2:29])=[O:26])[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 56960209HCID 56960209, compound

Product 1

HCID 56960208HCID 56960208, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture compound 3 (0.2 g) and NH3 (7N in MeOH, 10 mL) was heated to 50° C. for 14 hours. After cooling to room temperature, the reaction was titrated with water, and the solid was collected, washed with water and dried to obtain compound 5 as a white solid (0.11 g, yield 60%): 1H-NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, 8.3 Hz), 8.25 (d, 1H, 8.3 Hz), 8.15 (br, 1H, NH), 8.01 (dt, 1H, 1.3 & 8.1 Hz), 7.86 (d, 2H, 8.9 Hz), 7.73 (dt, 1H, 1.3 & 8.1 Hz), 7.39-7.44 (m, 2H), 7.13-7.23 (m, 5H), 5.99 (br, 1H, NH); LC/MS: m/z=342.5 [M+H]+(Calc: 341.4).

Workup

  1. customthe solid was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9885e2f294794f02a1c0c91825622063
Source dataset
uspto-grants-2015_10
Patent number
US09168255B2

Reaction notes

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