Hydrazine → HCID 68183057, compound

HRID 1615551Notes

Reaction equation

HRID 1615551 reaction equation
[C:1]([C:3]1[C:4]([CH:19]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)[CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)=[C:5]([C:14](OCC)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].NN>C(O)C.C(Cl)Cl>[N:8]1([C:7]2[S:6][C:5]3[C:14](=[O:15])[NH:21][CH2:20][CH:19]([C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH:33]=4)[C:4]=3[C:3]=2[C:1]#[N:2])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 9321Hydrazine2×HCID 68182975HCID 68182975, compound

Product 1

HCID 68183057HCID 68183057, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-cyano-3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-(2-naphthyl)ethyl]-5-(morpholin-4-yl)thiophene-2-carboxylate (0.126 g, 0.223 mmol) in ethanol (4.0 mL) and methylene chloride (1.0 mL) was added hydrazine (23.3 mg, 0.727 mmol). After 40 h of stirring at rt, hydrazine (25 mg, 0.78 mmol) was added and the mixture was stirred at rt for another 22 h. The mixture was filtered and concentrated. Purification on a silica gel column (continuous gradient of MeOH/DCM 0-20%) to afford a white solid product (0.0672 g, yield 77.1%). LCMS: (FA) ES+ 390. 1H NMR (400 MHz, d-chloroform) δ: 7.86-7.71 (m, 3H), 7.59 (s, 1H), 7.50-7.42 (m, 2H), 7.37 (dd, J=8.5, 1.8 Hz, 1H), 5.79 (d, J=4.0 Hz, 1H), 4.32 (d, J=3.5 Hz, 1H), 4.19-4.07 (m, 1H), 3.85-3.74 (m, 4H), 3.62 (ddd, J=12.5, 4.5, 2.3 Hz, 1H), 3.59-3.51 (m, 4H).

Workup

  1. stirringthe mixture was stirred at rt for another 22 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customPurification on a silica gel column (continuous gradient of MeOH/DCM 0-20%)

Sources & evidence

ORD record
ord-ab07f7c4c01746a9889189aec4bf2eb5
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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