Chlorosulfonic acid → HCID 59850053, compound

HRID 333688Notes

Reaction equation

HRID 333688 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]([C@H:17]([CH3:32])[C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]1)=[O:19])[CH2:12][CH2:11][CH2:10]2>>[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]([C@H:17]([CH3:32])[C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:26]3[CH:27]=[CH:28][C:29]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:30][CH:31]=3)[CH2:24][CH2:25]1)=[O:19])[CH2:12][CH2:11][CH2:10]2

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 59850056HCID 59850056, compound

Product 1

HCID 59850053HCID 59850053, compound

Procedure

After cooling chlorosulfonic acid (5.5 ml, 3 eq) to 0° C. under N2, (R)-2-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)-1-(4-phenylpiperazin-1-yl)propan-1-one (1 g, 2.72 mmol) was added and then allowed to warm up to rt. The solution was poured into an ice-water mixture (250 ml), followed by an extraction with CH2Cl2 (3×100 mL). The organic layer was dried over MgSO4 and evaporated in vacuo. The crude product was used without further purification for next step. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=466.3; tR=3.49 min.

Workup

  1. extractionfollowed by an extraction with CH2Cl2 (3×100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe crude product was used without further purification for next step

Sources & evidence

ORD record
ord-1b38ef2d778d477f8a765572f3395903
Source dataset
uspto-grants-2014_11
Patent number
US08883766B2

Reaction notes

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