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Hydrochloric Acid → 3-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride

HRID 1877809
Notes
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Reaction equation

HRID 1877809 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH2:14][CH2:13]3)[C:9]3=[CH:25][C:26]([CH3:28])=[CH:27][N:8]3[CH2:7][C:6]=2[CH:29]=1.O1CCOCC1.[ClH:36]>C(O)(C)C>[ClH:1].[ClH:36].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH2:16][CH2:17]3)[C:9]3=[CH:25][C:26]([CH3:28])=[CH:27][N:8]3[CH2:7][C:6]=2[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 601485641-Piperazinepropanoic acid, 4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)-alpha,alpha-dimethyl-

Product 1

HCID 601521963-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochlorideYield 188.7%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Procedure

To a suspension of 3-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid (24.25 g, 58.44 mmoles) in isopropyl alcohol (250 mL) at 60° C., add a 4M dioxane solution of hydrogen chloride (2.4 equiv; 35.07 mL, 140.26 mmoles) over 10 minutes to give a clear solution. Allow to cool slightly then evaporate to an off-white solid. Triturate with a small amount of diethyl ether and collect the powdery cream solid by filtration. Dry in a vacuum oven at 40° C. overnight. Grind to a fine powder and dry in a vacuum oven at 60° C. for 6 h. Monitor levels of residual isopropyl alcohol by 1H NMR. Dissolve in warm ethanol (350 mL) and evaporate to dryness. Triturate with ethanol (50 mL) and evaporate to dryness again. Triturate with dry diethyl ether (200 mL) and collect the resulting solid by filtration. Dry for 6 h in a vacuum oven at 50° C. to give 3-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride (26.9 g, 94% yield) MS (m/z): 415.2 (M+1).

Workup

  1. customto give a clear solution
  2. temperatureto cool slightly
  3. customthen evaporate to an off-white solid
  4. customTriturate with a small amount of diethyl ether
  5. customcollect the powdery cream solid
  6. filtrationby filtration
  7. customDry in a vacuum oven at 40° C. overnight
  8. customGrind to a fine powder
  9. customdry in a vacuum oven at 60° C. for 6 h
  10. dissolutionDissolve in warm ethanol (350 mL)
  11. customevaporate to dryness
  12. customTriturate with ethanol (50 mL)
  13. customevaporate to dryness again
  14. customTriturate with dry diethyl ether (200 mL)
  15. customcollect the resulting solid
  16. filtrationby filtration
  17. customDry for 6 h in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-497dd7f4fc6e4d2fb45f8b2d7590edd9
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314092B2

Reaction notes

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