Hydrazine hydrate (1:1) → HCID 131736921, compound

HRID 56390Notes

Reaction equation

HRID 56390 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C@H:24]1[C@@H:28]([N:29]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:27][C@@H:26]([C:40]([O:42][CH3:43])=[O:41])[CH2:25]1)[N:17]=[CH:16]2.O.NN>CCO>[NH2:29][C@@H:28]1[C@H:24]([NH:23][C:18]2[N:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:3]4[C:4]([Cl:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=4[Cl:1])[CH:14]=3)[N:19]=2)[CH2:25][CH:26]([C:40]([O:42][CH3:43])=[O:41])[CH2:27]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118037483HCID 118037483, compound

Product 1

HCID 131736921HCID 131736921, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1S,3R,4S)-methyl 3-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-4-(1,3-dioxoisoindolin-2-yl)cyclopentanecarboxylate (0.500 g, 0.805 mmol) was taken up in EtOH (20 ml) and hydrazine monohydrate (0.079 ml, 1.61 mmol) was added. The reaction was stirred overnight at room temperature. A white precipitate was filtered off and solvent was removed under reduced pressure. The precipitate was triturated with ether, followed by removal of the solvent under reduced pressure to give methyl (3S,4R)-3-amino-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclopentane-1-carboxylate (0.395 g, 0.805 mmol) in quantative yield, which was carried on without further purification. MS (ES+) C23H24Cl2N4O4 requires: 491, found: 492 [M+H]+.

Workup

  1. filtrationA white precipitate was filtered off
  2. customsolvent was removed under reduced pressure
  3. customThe precipitate was triturated with ether
  4. customfollowed by removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-512982171a4b4acc9f6f81dbd8983467
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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