Sodium Hydroxide → 3-(4-(5-Chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyrimidin-2-ylamino)benzenesulfonamide

HRID 1875423Notes

Reaction equation

HRID 1875423 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([C:14](=O)/[CH:15]=[CH:16]/N(C)C)=[CH:9][N:10]([CH2:11][CH2:12][CH3:13])[C:5]2=[C:4]([CH3:21])[CH:3]=1.Cl.[NH:23]([C:27]1[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)[C:24]([NH2:26])=[NH:25].[OH-].[Na+]>COCCO>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([C:14]3[CH:15]=[CH:16][N:26]=[C:24]([NH:23][C:27]4[CH:28]=[C:29]([S:33]([NH2:36])(=[O:34])=[O:35])[CH:30]=[CH:31][CH:32]=4)[N:25]=3)=[CH:9][N:10]([CH2:11][CH2:12][CH3:13])[C:5]2=[C:4]([CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 86658647(E)-1-(5-chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-oneHCID 178479386HCID 178479386, compound

Product 1

HCID 584829513-(4-(5-Chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyrimidin-2-ylamino)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (E)-1-(5-chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one (0.2 mmol), 3-guanidinobenzenesulfonamide hydrochloride (0.5 mmol) and NaOH (0.8 mmol) in 3 mL of 2-methoxyethanol was heated in a Microwave at 150° C. for 30 minutes. The reaction mixture was purified by column chromatography using EtOAc/PE (1:1, v/v) to elute 3-(4-(5-chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyrimidin-2-ylamino)benzenesulfonamide which was re-crystallised from EtOAc to give white solid. 1H-NMR (DMSO-d6) δ: 0.92 (t, 3H, J=7.2 Hz, CH3), 1.87 (m, 2H, CH2), 4.42 (t, 2H, J=7.2 Hz, CH2), 7.19 (s, 1H, Ar—H or Ph-H), 7.34 (s, 2H, NH2), 7.43 (m, 1H, Ar—H or Ph-H), 7.49 (t, 1H, J=7.6 Hz, Ph-H), 7.62 (m, 1H, Ph-H), 8.02 (d, 1H, J=4.8 Hz, Pyrimidin-H), 8.55 (d, 1H J=5.2 Hz, Pyrimidin-H), 8.63 (s, 1H, Ar—H), 9.92 (s, 1H, NH). MS (ESI+) m/z 457.1245 (M+H)+.

Workup

  1. customThe reaction mixture was purified by column chromatography
  2. washv/v) to elute 3-(4-(5-chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyrimidin-2-ylamino)benzenesulfonamide which
  3. customwas re-crystallised from EtOAc
  4. customto give white solid

Sources & evidence

ORD record
ord-8bbbc996fc154bc0b7df0d0ca63a250d
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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