Dichloromethane → HCID 59627863, compound

HRID 1256664Notes

Reaction equation

HRID 1256664 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(Cl)Cl.S(Cl)(Cl)=O.[CH2:21]([O:28][C:29](=[O:44])[NH:30][C:31]1[C:32]([NH2:43])=[N:33][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][CH:36]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:28][C:29](=[O:44])[NH:30][C:31]1[C:32]([NH:43][C:9](=[O:11])[C:8]2[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=2)=[N:33][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][CH:36]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 19266p-Acetamidobenzoic acidHCID 24386Thionyl ChlorideHCID 59627856HCID 59627856, compound

Product 1

HCID 59627863HCID 59627863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(acetylamino)benzoic acid (33.6 mg, 0.188 mmol) and methylene chloride (0.190 mL) was cooled to 0° C. and treated with thionyl chloride (41 uL, 0.563 mmol) and a drop of DMF. The cold bath was removed, and the reaction progress was checked via piperidine quench and LCMS. The reaction was thoroughly concentrated and dissolved in methylene chloride:THF (1:1, 0.240 mL) and benzyl(2-amino-6-phenylpyridin-3-yl)carbamate (20 mg, 0.0626 mmol) added. After 2 days the reaction was concentrated, taken into DMF and purified via reversed phase HPLC, 20-80% MeCN in water with 0.05% TFA to afford the requisite compound which was taken to the next reaction. MS cal'd 481 (M+H)+, exp 481 (M+H)+.

Workup

  1. customThe cold bath was removed
  2. customquench
  3. concentrationThe reaction was thoroughly concentrated
  4. dissolutiondissolved in methylene chloride:THF (1:1, 0.240 mL)
  5. concentrationAfter 2 days the reaction was concentrated
  6. custompurified via reversed phase HPLC, 20-80% MeCN in water with 0.05% TFA
  7. customto afford the requisite compound which
  8. customwas taken to the next reaction

Sources & evidence

ORD record
ord-925f85e197da4df7a8df6f6b1a9ad7f9
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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