Hydrazine → HCID 57947596, compound

HRID 340956Notes

Reaction equation

HRID 340956 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:45])[O:14][CH2:15][C@@H:16]([N:31]([CH3:44])[C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=1[Cl:43])=[O:33])[CH2:17][CH2:18][CH2:19][N:20]1C(=O)C3C(=CC=CC=3)C1=O)=[CH:5]2.NN>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:45])[O:14][CH2:15][C@@H:16]([N:31]([CH3:44])[C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=1[Cl:43])=[O:33])[CH2:17][CH2:18][CH2:19][NH2:20])=[CH:5]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57947727HCID 57947727, compound

Product 1

HCID 57947596HCID 57947596, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(1,3-dioxoisoindolin-2-yl)pentyl 6-fluoroisoquinolin-3-ylcarbamate (400 mg, 0.64 mmol) in MeOH (10.0 mL) was added NH2NH2 (1.0 mL). The reaction mixture was stirred at RT for 2 h. The mixture was concentrated and re-dissolved in MeOH. The mixture was filtered and purified on RP-HPLC using a mixture of acetonitrile and water to give (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 6-fluoroisoquinolin-3-ylcarbamate (305 mg, quant.). LRMS (M+H+) m/z 506.2.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionre-dissolved in MeOH
  3. filtrationThe mixture was filtered
  4. custompurified on RP-HPLC
  5. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-f87a7bfb5e2e411fb840340ca35835b1
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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