Trifluoroacetic acid → HCID 86618257, compound

HRID 1159817Notes

Reaction equation

HRID 1159817 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:21][N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[CH:6]2.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>ClCCl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[CH3:1][O:2][C:3]1[C:4]([CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:13])=[O:14])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86618255HCID 86618255, compound2×

Product 1

HCID 86618257HCID 86618257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-{[5-methoxy-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylate (0.050 g, 0.102 mmol, Intermediate 76) was dissolved in dichloromethane (4 mL) and TFA (1 mL) was added. The mixture was stirred and rt for 2 h and evaporated. The crude product was purified by reversed phase preparative HPLC using ACE Prep UV C8 150×30 mm, flow 38 mL/min, gradient time 8.5 min using the eluent system: water/0.1% TFA and CH3CN (20-40% MeCN), fractions collected based on UV-signal (254 nm). The purest fractions were pooled and the acetonitrile was evaporated. Yield: 29 mg (46%). Brown liquid, off white solid after 1 h. Isolated as the TFA salt. MS (ESI+) for C20H23N3O3S m/z 386.4 (M+H)+.

Workup

  1. customevaporated
  2. customThe crude product was purified by reversed phase preparative HPLC
  3. custom38 mL/min, gradient time 8.5 min
  4. customwater/0.1% TFA and CH3CN (20-40% MeCN), fractions collected
  5. customthe acetonitrile was evaporated
  6. waitBrown liquid, off white solid after 1 h

Sources & evidence

ORD record
ord-452de981a2974fd79b6dde4adf4597cf
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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