Benzyl Alcohol → HCID 67023641, compound

HRID 491907Notes

Reaction equation

HRID 491907 reaction equation
[NH2:1][C:2]1[N:3]([C@H:19]([CH:25]2[CH2:30]CCC[CH2:26]2)[CH2:20][CH2:21][C:22](O)=[O:23])[CH2:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=[CH:8][C:6]=2[N:7]=1.C(Cl)(=O)C(Cl)=O.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[CH2:37]([O:44][C:22](=[O:23])[CH2:21][CH2:20][CH:19]([N:3]1[CH2:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:9]=[CH:8][C:6]=2[N:7]=[C:2]1[NH2:1])[CH:25]([CH3:30])[CH3:26])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 65578Oxalyl chlorideHCID 57678358HCID 57678358, compound

Product 1

HCID 67023641HCID 67023641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(2-amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-4-(S)-cyclohexyl-butyric acid (0.1 g, 0.25 mmol) in DCM (10 mL) was added oxalyl chloride (2.0M in DCM, 0.8 mL, 2 mmol). The resulting mixture was stirred at room temperature one hour. An aliquot from the reaction mixture was quenched in MeOH and analyzed by MS-HPLC which indicated that all of the acid was converted to the corresponding acid chloride. The solvent and excess oxalyl chloride was removed by vacuum. DCM (10 mL) was added followed by benzyl alcohol (0.089 mL, 0.8 mmol). The resulting solution was stirred at room temperature for one hour. The solvent was removed under vacuum to yield an oil which was purified by Gilson HPLC to yield the title compound as a solid, as its corresponding TFA salt.

Workup

  1. customAn aliquot from the reaction mixture was quenched in MeOH
  2. customThe solvent and excess oxalyl chloride was removed by vacuum
  3. additionDCM (10 mL) was added
  4. stirringThe resulting solution was stirred at room temperature for one hour
  5. customThe solvent was removed under vacuum
  6. customto yield an oil which
  7. customwas purified by Gilson HPLC

Sources & evidence

ORD record
ord-9c525b6c2ba44f72a37d839f20b709af
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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