Methanol → HCID 11983345, compound

HRID 2301858Notes

Reaction equation

HRID 2301858 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=1.C1(OP(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.[NH2:32][C@@H:33]1[CH:38]2[CH2:39][CH2:40][N:35]([CH2:36][CH2:37]2)[CH2:34]1.CO>C(Cl)Cl.CN(C=O)C.CN(C=O)C>[N:35]12[CH2:40][CH2:39][CH:38]([CH2:37][CH2:36]1)[C@@H:33]([NH:32][C:12]([C:10]1[S:11][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][CH:9]=1)=[O:14])[CH2:34]2

Participants

7

Reactant 4

HCID 887MethanolHCID 75654Diphenyl chlorophosphateHCID 719215(3R)-1-Azabicyclo(2.2.2)octan-3-amineHCID 7364825-(Pyridin-2-yl)thiophene-2-carboxylic acid

Product 1

HCID 11983345HCID 11983345, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

TEA (50 μL, 0.35 mmol) is added to a suspension of 5-(pyridin-2-yl)-2-thiophenecarboxylic acid (72 mg, 0.35 mmol) in CH2Cl2:DMF (2:1, 1.5 mL). Diphenylchlorophosphate (62 μL, 0.3 mmol) is added and the resulting solution is stirred at room temperature for 30 minutes. A solution of (R)-3-aminoquinuclidine (1M, 0.2 mmol, 0.2 μL) in DMF is added and the resulting solution is stirred overnight at room temperature. MeOH is added and the mixture is poured through a column of AG50Wx2 ion exchange resin (H+ form). The resin is washed with MeOH then the product is eluted with 5% TEA in MeOH. The eluent is evaporated to dryness to yield the desired product (15 mg, 24%). MS for C17H19N3OS (EST (M+H)+ m/z 314.

Workup

  1. stirringthe resulting solution is stirred overnight at room temperature
  2. additionthe mixture is poured through a column of AG50Wx2 ion exchange resin (H+ form)
  3. washThe resin is washed with MeOH
  4. washthe product is eluted with 5% TEA in MeOH
  5. customThe eluent is evaporated to dryness

Sources & evidence

ORD record
ord-0ba95df12674439cae0f62ac42fe7f0a
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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