Dimethylformamide → HCID 67093846, compound

HRID 593621Notes

Reaction equation

HRID 593621 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-9bfe6d88a8604e719d6437e919a16ff1
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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