Water → HCID 16113673, compound

HRID 2245502Notes

Reaction equation

HRID 2245502 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[C:14]([C:18]1[CH:34]=[CH:33][C:21]([CH2:22][N:23]2[C:31]3[C:26](=[CH:27][C:28]([NH2:32])=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.O>CC(C)=O.CC#N>[C:14]([C:18]1[CH:34]=[CH:33][C:21]([CH2:22][N:23]2[C:31]3[C:26](=[CH:27][C:28]([NH:32][S:2]([C:5]4[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=4)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 81531DiisopropylethylamineHCID 43165373HCID 43165373, compound

Product 1

HCID 16113673HCID 16113673, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3-chlorosulfonyl-benzoic acid (0.80 g, 0.36 mmol) was added in one portion to 1-(4-tert-butylbenzyl)-5-amino-1H-indole (0.30 g, 1.08 mmol) and diisopropylethylamine (0.25 g, 0.90 mmol) in acetone (25 ml) at 0° C. under a nitrogen atmosphere. The resulting yellow solution was stirred at 0° C. for 5 minutes and then stirred for 3 hours at room temperature. The reaction was quenched with water (2 ml) and concentrated in vacuo to a brown powder. The powder was partitioned between EtOAc (15 ml) and std NaHCO3 (10 ml). All organics were combined, extracted with water (10 ml) and brine (10 ml), dried with MgSO4, filtered and concentrated in vacuo to afford a brown powder. This brown powder was subjected to gradient RP-HPLC (H2O: CH3CN) and the title compound was isolated as a brown powder (0.36 g, 8.6% yield): MS (ESI) m/z 463, MS (ESI) m/z 461.

Workup

  1. stirringstirred for 3 hours at room temperature
  2. customThe reaction was quenched with water (2 ml)
  3. concentrationconcentrated in vacuo to a brown powder
  4. customThe powder was partitioned between EtOAc (15 ml) and std NaHCO3 (10 ml)
  5. extractionextracted with water (10 ml) and brine (10 ml)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a brown powder

Sources & evidence

ORD record
ord-73f19463617e4ad9a9838992c008e3e1
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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