Dimethylformamide → HCID 67093846, compound

HRID 1661666Notes

Reaction equation

HRID 1661666 reaction equation
[CH3:1][S:2]([C:5]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([NH2:22])[C:6]1[CH:7]=[C:8]([C:12]2[N:13]([CH3:21])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[N:10][CH:11]=1)(=[O:4])=[O:3].ClS([N:34]=[C:35]=O)(=O)=O.CN(C=O)C>ClCCl>[CH3:1][S:2]([C:5]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([NH2:22])[C:6]1[CH:7]=[C:8]([C:12]2[N:13]([CH3:21])[C:14]3[C:19]([C:20]=2[C:35]#[N:34])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[N:10][CH:11]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 67093635HCID 67093635, compound

Product 1

HCID 67093846HCID 67093846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-indole (350 mg, 0.842 mmol) in dichloromethane (10 mL) is added chlorosulfonyl isocyanate (0.358 g, 2.53 mmol). The mixture is stirred at ambient temperature for 20 min, whereupon anhydrous DMF (2 mL) is added. After 1 h, the mixture is concentrated to a volume of 3 mL, and filtered. Purification by RP HPLC affords 2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-3-cyano-indole. MS (ESI) m/z 441.1 (M+H)+.

Workup

  1. additionis added
  2. concentrationthe mixture is concentrated to a volume of 3 mL
  3. filtrationfiltered
  4. customPurification by RP HPLC

Sources & evidence

ORD record
ord-2c5312791f324c128148df78f2847171
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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