HCID 178513489, compound → HCID 178513488, compound

HRID 64334Notes

Reaction equation

HRID 64334 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]2[NH:8][C:9]3[N:10]([N:11]=[C:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:19][CH:18]=4)[C:13]=3[C:14]([NH2:16])=[O:15])[C:6]=2[CH:5]=1)([O-])=O>CC(O)=O.[Zn]>[NH2:1][C:4]1[CH:31]=[CH:30][C:7]2[NH:8][C:9]3[N:10]([N:11]=[C:12]([C:17]4[CH:18]=[CH:19][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:21][CH:22]=4)[C:13]=3[C:14]([NH2:16])=[O:15])[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 178513489HCID 178513489, compound

Product 1

HCID 178513488HCID 178513488, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 7-nitro-2-(4-phenoxyphenyl)-4H-benzo[4,5]imidazo[1,2-b]pyrazole-3-carboxamide (9 mg, 0.022 mmol) in 3 mL of HOAc was added zinc powder (14 mg, 0.22 mmol). Then the mixture was stirred at RT for 20 min, until TLC and LCMS analysis showed that most of starting material was consumed. The reaction solid was filtered off. The filtrate was concentrated, suspended in 10 mL of EA and filtered. The filtrate was concentrated to get the product as a white solid (4 mg, 50%). 1H NMR (400 MHz, CD3OD-d4) δ 7.60 (d, J=8.6 Hz, 2H), 7.32 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.16 (s, 1H), 7.08 (t, J=8.0 Hz, 1H), 7.05-6.95 (m, 4H), 6.79 (dd, J=1.6, 8.4 Hz, 1H). MS (ESI) m/e [M+1]+ 384.

Workup

  1. customwas consumed
  2. customThe reaction solid
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-49ef5432deec4cc8863f7805e7cf972b
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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