Acetic Acid → HCID 44553896, compound

HRID 1254057Notes

Reaction equation

HRID 1254057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:33]=[CH:32][C:24]([C:25](/[N:27]=[CH:28]/[N:29](C)C)=O)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.C(O)(=O)C.[NH2:38]N>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:33]=[CH:32][C:24]([C:25]3[NH:38][N:29]=[CH:28][N:27]=3)=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 178484328HCID 178484328, compound

Product 1

HCID 44553896HCID 44553896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the crude product of Step 1, 2 mL of acetic acid and 0.15 mL of anhydrous hydrazine was stirred at 90° C. for 30 min. The reaction mixture was diluted with MeOH and was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, (CD3OD): 8.08 (s, 1H), 8.05 (m, 4H), 7.73 (m, 2H), 7.58 (m, 3H), 7.35 (d, 2H), 7.11 (d, 2H), 3.68 (s, 3H), 1.61 (s, 6H). LCMS: m/z 421 (M+H)+.

Workup

  1. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-cbf8a57cec044bed831ac889f4c0d3c5
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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