Hydrochloric Acid → HCID 66826119, compound

HRID 2177973Notes

Reaction equation

HRID 2177973 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([N+:12]([O-:14])=[O:13])[C:6]([OH:11])=[C:7]([CH:10]=1)[C:8]#[N:9])=O.[C:15]1([C:21](=O)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH2:30][C:31]([NH2:33])=[O:32].Cl>C(O)C>[OH:11][C:6]1[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([CH:1]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:33][C:31](=[O:32])[NH:30]2)=[CH:10][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 86669351HCID 86669351, compound2×

Product 1

HCID 66826119HCID 66826119, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-formyl-2-hydroxy-3-nitrobenzonitrile (Intermediate 61) (150 mg, 0.78 mmol), 1,2-diphenylethanone (153 mg, 0.78 mmol), urea (141 mg, 2.34 mmol), conc. hydrochloric acid (0.5 mL) in ethanol (3 mL) was refluxed for 37 hours. The mixture was evaporated and purified by prep.-HPLC (0.1% TFA as additive) to give Compound 122 (51 mg, yield 16%). HNMR (DMSO-d6, 400 MHz): δ 8.77 (s, 1H), 8.16 (d, J=2.0 Hz, 1H), 7.92 (d, J=2.4 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.25-7.21 (m, 5H), 7.01-6.98 (m, 3H), 6.82-6.79 (m, 2H), 5.31 (d, J=2.8 Hz, 1H), MS (ESI): m/z 413.0 [M+H]+.

Workup

  1. temperaturewas refluxed for 37 hours
  2. customThe mixture was evaporated
  3. custompurified by prep.-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-0bf98850c8ab46ba94818a940286bd83
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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