Hydrazine → HCID 67317119, compound

HRID 533282Notes

Reaction equation

HRID 533282 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]/[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=2)[N:20]([CH2:28][CH2:29][CH2:30][O:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)[C:19]=1[C:42]([O:44]CC)=[O:43].NN>O1CCCC1.C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=2)[N:20]([CH2:28][CH2:29][CH2:30][O:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)[C:19]=1[C:42]([OH:44])=[O:43]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 86630291(E)-ethyl 3-(6-(1,3-dioxoisoindolin-2-yl)hex-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 67317119HCID 67317119, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-ethyl 3-(6-(1,3-dioxoisoindolin-2-yl)hex-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (The synthesis of this compound was described in EXAMPLE 160B as an intermediate.) (270 mg) and hydrazine (0.030 ml) in tetrahydrofuran (1.00 ml) and ethanol (3 ml) was heated at 50° C. overnight and concentrated. The residue was dissolved in tetrahydrofuran and methanol and then aqueous 10% NaOH was added. The resulting was heated at 50° C. overnight and concentrated. The residue was purified by RPHPLC to provide the title compound. 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ 8.17 (dd, J=8.44, 1.07 Hz, 1H), 7.84-7.89 (m, 1H), 7.60 (dd, J=9.21, 4.30 Hz, 1H), 7.41-7.56 (m, 4H), 7.32-7.40 (m, 1H), 7.01-7.11 (m, 1H), 6.84 (d, J=7.06 Hz, 1H), 4.80 (t, J=7.21 Hz, 2H), 4.12 (t, J=5.83 Hz, 2H), 2.94-3.06 (m, 2H), 2.75 (t, J=8.29 Hz, 2H), 2.20-2.35 (m, 2H), 1.43-1.63 (m, 4H), 1.27-1.36 (m, 4H).

Workup

  1. customThe synthesis of this compound
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in tetrahydrofuran
  4. additionmethanol and then aqueous 10% NaOH was added
  5. concentrationconcentrated
  6. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-5273599b3a2144ad861c81ea1f231c63
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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