Triethylamine → HCID 178436776, compound

HRID 1509050Notes

Reaction equation

HRID 1509050 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][OH:24])=[NH:22])=[CH:16][CH:15]=3)[C:10]([CH2:25][CH3:26])=[C:9]([CH3:27])[N:8]=2)=[CH:4][CH:3]=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30].CCN(CC)CC>ClCCl>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20]/[C:21](=[N:22]\[C:29](=[O:30])[O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)/[NH:23][OH:24])=[CH:18][CH:19]=3)[C:10]([CH2:25][CH3:26])=[C:9]([CH3:27])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 178436777HCID 178436777, compound

Product 1

HCID 178436776HCID 178436776, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 18-mL vial was charged with 2-[4-[[2-(5-Chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]-N-hydroxy-acetamidine (61 mg, 0.15 mmol), phenyl chloroformate (29 mg, 0.18 mmol, 1.2 eq.), Et3N (20 mg, 0.2 mmol, 1.3 eq.) and dichloromethane (5 ml). The mixture was stirred at 0 C˜rt until starting material was consumed (4 hr). The mixture was poured into saturated sodium bicarbonate solution (10 ml) and extracted with dichloromethane (3×5 ml). The organic layers were combined and dried over Na2SO4. Removal of solvent under reduced pressure gave the title compound (80 mg, 100% yield). The product thus obtained was forwarded to the next step without any purification.

Workup

  1. customwas consumed (4 hr)
  2. additionThe mixture was poured into saturated sodium bicarbonate solution (10 ml)
  3. extractionextracted with dichloromethane (3×5 ml)
  4. dry with materialdried over Na2SO4
  5. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-7ef325a66b754615ae6c151f310ce599
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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