Hydrochloric Acid → HCID 59534637, compound

HRID 593644Notes

Reaction equation

HRID 593644 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:36]#[N:37])=[C:7]([C:12]3[CH:13]=[C:14]([CH2:18][NH:19][S:20]([CH2:23][CH2:24][N:25]4C(=O)C5C(=CC=CC=5)C4=O)(=[O:22])=[O:21])[CH:15]=[N:16][CH:17]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1.NN.Cl>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:36]#[N:37])=[C:7]([C:12]3[CH:13]=[C:14]([CH2:18][NH:19][S:20]([CH2:23][CH2:24][NH2:25])(=[O:22])=[O:21])[CH:15]=[N:16][CH:17]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 59534638HCID 59534638, compound

Product 1

HCID 59534637HCID 59534637, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask is charged with 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide (0.065 g, 0.109 mmol) and MeOH (4 mL). Hydrazine (0.069 mL, 2.183 mmol) is added and the reaction is stirred at room temperature overnight. 2M aqueous HCl is added, followed by concentration in vacuo. Dichloromethane is added and the mixture is filtered through celite. The organic layer is washed with water once and the aqueous layer is basified to using 4M aqueous NaOH and extracted with dichloromethane thrice. The combined dichloromethane fraction is dried over sodium sulfate and concentrated in vacuo to afford a residue which is purified by reverse-phase HPLC to afford 2-amino-ethanesulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide as a solid. 1H NMR (400 MHz, MeOD) δ ppm 3.12 (t, J=6.6 Hz, 2H), 3.29 (t, J=6.6 Hz, 2H), 3.84 (s, 3H), 4.49 (s, 2H), 7.38 (dd, J=8.6, 1.8 Hz, 1H), 7.73 (d, J=8.6 Hz, 1H), 7.78 (d, J=1.5 Hz, 1H), 8.19 (t, J=2.1 Hz, 1H), 8.81 (d, J=2.3 Hz, 1H), 8.82 (d, J=2.3 Hz, 1H). HRMS (ESI) m/z 404.0944 [(M+H)+ Calcd for C18H19ClN5O2S: 404.0948].

Workup

  1. concentrationfollowed by concentration in vacuo
  2. additionDichloromethane is added
  3. filtrationthe mixture is filtered through celite
  4. washThe organic layer is washed with water once
  5. extractionextracted with dichloromethane thrice
  6. dry with materialThe combined dichloromethane fraction is dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a residue which
  9. customis purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-70ea10d8085e4cb29efd085687727509
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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