N'-Hydroxycyclopropanecarboximidamide → HCID 53984799, compound

HRID 867557Notes

Reaction equation

HRID 867557 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16](O)=[O:17])=[C:5]2[C@@H:4]2[CH2:19][CH2:20][CH2:21][N:3]12.[CH:22]1([C:25](=[N:27]O)[NH2:26])[CH2:24][CH2:23]1>CN(C)C=O>[CH:22]1([C:25]2[N:27]=[C:16]([C:15]3[N:14]=[CH:13][N:6]4[C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=5[C:2](=[O:1])[N:3]5[CH2:21][CH2:20][CH2:19][C@H:4]5[C:5]=34)[O:17][N:26]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 54415726HCID 54415726, compound

Product 1

HCID 53984799HCID 53984799, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.70 g (2.72 mmol) of (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid in 40 ml of N,N-dimethylformamide are stirred at room temperature for 10 minutes and at 85° for 20 minutes with 4.41 g (27.2 mmol) of N,N'-carbonyldiimidazole. 2.72 g (27.2 mmol) of cyclopropanecarboxamidoxime are subsequently added thereto and the mixture is stirred at 110° for a further hour. After removing the N,N-dimethylformamide the residue is stirred in 30 ml of acetic acid at 120° for 4 hours. The solution is evaporated and the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic phase is separated, dried over magnesium sulphate and evaporated. By recrystallization from ethyl acetate there is obtained (S)-1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 211°-212°.

Workup

  1. customAfter removing the N,N-dimethylformamide the residue
  2. stirringis stirred in 30 ml of acetic acid at 120° for 4 hours
  3. customThe solution is evaporated
  4. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-94d3615dd4f84059bc74495d07e35222
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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