Ethanol → HCID 86681374, compound

HRID 1406673Notes

Reaction equation

HRID 1406673 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=2[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21](OCC)=[O:22])[CH2:16][CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:30][NH2:31].C(O)C>CO>[C:1]1([S:7]([CH2:10][C:11]2[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=2[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]([NH:30][NH2:31])=[O:22])[CH2:16][CH2:15]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 86681373HCID 86681373, compound

Product 1

HCID 86681374HCID 86681374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesized according to General Procedure C: 6{29} (1.16 g, 2.77 mmol, 1 equiv.), anhydrous hydrazine (0.26 mL, 8.32 mmol, 3 equiv.), ethanol (15.6 mL), methanol (10 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{29} (0.88 g, 79%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 8.10 (br s, 1H), 7.66 (dd, 2H, J=0.5, 8.0 Hz), 7.64-7.61 (m, 1H), 7.47 (t, 2H, J=8.0 Hz), 7.24 (dt, 1H, J=1.0, 7.5 Hz), 7.17-7.12 (m, 2H), 6.95 (d, 1H, J=7.5 Hz), 4.80 (s, 2H), 3.83 (br s, 2H), 3.40 (s, 2H), 3.04 (s, 2H), 2.47 (br s, 4H), 2.35 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.4, 138.6, 138.0, 133.7, 132.6, 131.1, 128.9, 128.7, 128.5, 128.0, 127.5, 61.1, 60.5, 59.1, 53.6, 53.0.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{29} (0.88 g, 79%) as a white solid

Sources & evidence

ORD record
ord-13e828ac9c174338b2b6fd358fe0891f
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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