HCID 49832941, compound → HCID 59605616, compound

HRID 1946013Notes

Reaction equation

HRID 1946013 reaction equation
[CH3:1][C:2]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[N:17]([CH3:41])[C:18]3[C:23]([N:24]=2)=[C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:21]=[C:20]([N:31]2[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[N:33]=[C:32]2[CH3:40])[N:19]=3)[CH2:11][CH2:10]1)([CH3:8])[C:3]([O:5]CC)=[O:4]>[Li+].[OH-].C1COCC1>[CH3:8][C:2]([N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[N:17]([CH3:41])[C:18]3[C:23]([N:24]=2)=[C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:21]=[C:20]([N:31]2[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[N:33]=[C:32]2[CH3:40])[N:19]=3)[CH2:13][CH2:14]1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 49832941HCID 49832941, compound

Product 1

HCID 59605616HCID 59605616, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-methyl-2-(4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperazin-1-yl)propanoate 507 (0.14 g, 0.25 mmol) in 2M LiOH (5.0 mL) and THF (8 mL) was stirred at reflux for 18 hours. The reaction was then cooled to room temperature and concentrated down to ⅓ of original volume. The residue was then loaded onto a SCX-2 column. The column was first washed with MeOH. The product was then eluted with 2M NH3 in MeOH and then concentrated. The residue was purified by RP-HPLC to give 506. LCMS m/z: 534.3 (MH+)

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated down to ⅓ of original volume
  3. washThe column was first washed with MeOH
  4. washThe product was then eluted with 2M NH3 in MeOH
  5. concentrationconcentrated
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-b21f715d1d8b42a19c2fac035870fd2e
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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