Hydrazine → (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-chloropyridin-2-ylcarbamate

HRID 416390Notes

Reaction equation

HRID 416390 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[O:10][CH2:11][C@@H:12]([N:27]([CH3:40])[C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[Cl:39])=[O:29])[CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[N:6][CH:7]=1.NN>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[O:10][CH2:11][C@@H:12]([N:27]([CH3:40])[C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[Cl:39])=[O:29])[CH2:13][CH2:14][CH2:15][NH2:16])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57947593(S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(1,3-dioxoisoindolin-2-yl)pentyl 5-chloropyridin-2-ylcarbamate

Product 1

HCID 57947748(S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-chloropyridin-2-ylcarbamateYield 73%

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 5-chloropyridin-2-ylcarbamate (280 mg, 0.47 mmol) in MeOH (5.0 mL) was added NH2NH2 (0.13 mL, 4.7 mmol). The reaction mixture was stirred at RT for 2 h. The mixture was concentrated and re-dissolved in MeOH. The resulting solution 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 5-chloropyridin-2-ylcarbamate (162 mg, 73%). LRMS (M+H+) m/z 472.2.

Workup

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

Sources & evidence

ORD record
ord-e2af8e8b227246b2bfd61e4a23e268ff
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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