(R)-3-Pyrrolidinol → HCID 135928899, compound

HRID 1685102Notes

Reaction equation

HRID 1685102 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8]([CH2:12]Cl)[NH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH:20]1[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]1>CO>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([CH2:12][N:20]3[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]3)[NH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 136406659HCID 136406659, compound

Product 1

HCID 135928899HCID 135928899, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of EXAMPLE 10A (90 mg, 0.25 mmol) in methanol (5 mL) was added (R)-pyrrolidin-3-ol (87 mg, 1 mmol) and the mixture stirred at ambient temperature for 2 days. The solvent was removed and residue purified by flash chromatography on silica gel using 1:10:0.5 methanol/ethyl acetate/concentrated ammonium hydroxide to give the title compound. 1H NMR (DMSO-d6) δ 7.75-7.77 (m, 2H), 7.54-7.59 (m, 3H), 4.85 (br, 1H), 4.20 (t, J=6.3 Hz, 1H), 3.69-3.75 (m, 2H), 2.81-2.86 (m, 2H), 2.57-2.58 (m, 2H), 2.01-2.08 (m, 1H), 1.59-1.65 (m, 1H).

Workup

  1. customThe solvent was removed
  2. customresidue purified by flash chromatography on silica gel using 1:10:0.5 methanol/ethyl acetate/concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-f0d332d3d3224eb59da8ccab8874a292
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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