1-(3-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamine → 3-[4-[3-(4-Aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]-N,N-dimethylbenzenemethanamine

HRID 28958Notes

Reaction equation

HRID 28958 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[N:21](S(C5C=CC=CC=5)(=O)=O)[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]([CH3:33])[CH3:32])[CH:25]=5)=[CH:23][C:16]=34)=[CH:13][N:12]([CH2:43][CH3:44])[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.[Zn]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[NH:21][C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]([CH3:32])[CH3:33])[CH:25]=5)=[CH:23][C:16]=34)=[CH:13][N:12]([CH2:43][CH3:44])[N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 689990361-(3-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamine

Product 1

HCID 689990183-[4-[3-(4-Aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]-N,N-dimethylbenzenemethanamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-[3-(4-nitrophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine (1.1 mmol) in HOAc (20 mL) was added portionwise zinc dust (8.0 mmol) over 5 minutes. The reaction was stirred at room temperature for 1 h, filtered through a pad of Celite, rinsed with acetic acid, and concentrated to dryness under vacuum. The residue was re-evaporated several times from methanol/toluene to remove the excess acetic acid, taken up in methanol (35 mL) and treated with 6 N sodium hydroxide (1.5 mL). The reaction mixture was stirred and heated at 70° C. for 8 h. After cooling to room temperature the reaction was concentrated under vacuum, triturated with cold water, filtered, washed with water, and dried under vacuum to give the crude product as a pale orange solid: ESMS [M+H]+: 437.2

Workup

  1. filtrationfiltered through a pad of Celite
  2. washrinsed with acetic acid
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue was re-evaporated several times from methanol/toluene
  5. customto remove the excess acetic acid
  6. additiontreated with 6 N sodium hydroxide (1.5 mL)
  7. stirringThe reaction mixture was stirred
  8. temperatureheated at 70° C. for 8 h
  9. temperatureAfter cooling to room temperature the reaction
  10. concentrationwas concentrated under vacuum
  11. customtriturated with cold water
  12. filtrationfiltered
  13. washwashed with water
  14. customdried under vacuum

Sources & evidence

ORD record
ord-64c3cfda40bb4f94a22bd086e664e3c6
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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