Hydrochloric Acid → HCID 86745073, compound

HRID 728668Notes

Reaction equation

HRID 728668 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[CH2:26][C@H:25]([CH2:27][OH:28])[CH:24]=[CH:23]2)=[C:15](Cl)[N:14]=1.[OH-].[Na+]>CO>[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[CH2:26][C@H:25]([CH2:27][OH:28])[CH:24]=[CH:23]2)=[C:15]([NH:10][C@@H:8]2[CH2:9][C@H:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19493(1R,2S)-TranylcypromineHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 86745073HCID 86745073, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of trans-2-phenyl cyclopropylamine.HCl (1.02 g, 6 mmol) in methanol (10 ml) was stirred with basic ion exchange resin for 5 minutes. The resin was filtered off and the filtrate was concentrated to a colorless oil. To this was added (±)-(cis)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.549 g, 2 mmol). The resulting solution was stirred in a Parr bomb at 80° C. for 12 hours 1 N NaOH 12 ml) was added and the solvent evaporated. The residual oil was chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform to give tan crystals after crystallization from acetonitrile-methanol (0.221 g, 30%), m.p.=188-190° C.

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe filtrate was concentrated to a colorless oil
  3. additionwas added
  4. customthe solvent evaporated
  5. customThe residual oil was chromatographed on silica gel
  6. washTitle compound was eluted with 5% methanol-chloroform
  7. customto give tan crystals
  8. customafter crystallization from acetonitrile-methanol (0.221 g, 30%), m.p.=188-190° C.

Sources & evidence

ORD record
ord-ba1e362cc73a41b6a09a31b2e6a85c5c
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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