Sulfuryl chloride → HCID 25069587, compound

HRID 1920766Notes

Reaction equation

HRID 1920766 reaction equation
[CH:1]1([CH2:7][C@H:8]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][C:18]2=[O:23])[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:24](Cl)(Cl)(=[O:26])=[O:25].CCN([CH:35]([CH3:37])[CH3:36])C(C)C>C(Cl)(Cl)Cl>[CH:1]1([CH2:7][C@H:8]([N:17]2[CH2:22][CH2:21][N:20]([S:24]([C:36]3[CH:35]=[CH:37][C:6]4[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=4)[CH:7]=3)(=[O:26])=[O:25])[CH2:19][C:18]2=[O:23])[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 81531DiisopropylethylamineHCID 57657406HCID 57657406, compound

Product 1

HCID 25069587HCID 25069587, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of compound 12F (16.8 mg, 0.05 mmol), sulfonyl chloride (0.06 mmol) and DIEA (17.4 μl, 0.10 mmol) in CHCl3 (200 μl) was maintained at ambient temperature for 30 minutes. Solvents were removed in vacuum. Residue was dissolved in 200 μl of DMSO and subjected to HPLC purification. [Chromolith SpeedRod RP-18e C18 column (4.6×50 mm); flow rate 1.5 ml/min; mobile phase A: 0.1% TFA/water; mobile phase B 0.1% TFA/ACN; gradient elution from 5% B to 100% B over 9.5 min, detection 254 nm]. Fractions containing the desired product were combined and dried to provide trifluoroacetic salt of target product.

Workup

  1. customSolvents were removed in vacuum
  2. dissolutionResidue was dissolved in 200 μl of DMSO
  3. customsubjected to HPLC purification
  4. wash[Chromolith SpeedRod RP-18e C18 column (4.6×50 mm); flow rate 1.5 ml/min; mobile phase A: 0.1% TFA/water; mobile phase B 0.1% TFA/ACN; gradient elution from 5% B to 100% B over 9.5 min, detection 254 nm]
  5. additionFractions containing the desired product
  6. customdried
  7. customto provide trifluoroacetic salt of target product

Sources & evidence

ORD record
ord-37315806781c48738cb32632a477f8d6
Source dataset
uspto-grants-2012_05
Patent number
US08173645B2

Reaction notes

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