Hydrochloric Acid → HCID 9884048, compound

HRID 864376Notes

Reaction equation

HRID 864376 reaction equation
Cl.[OH-:2].[Na+].[CH3:4][N:5]([CH2:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH3:6].[C:17]1(C)[C:18](C)=[CH:19][CH:20]=[CH:21][CH:22]=1>O>[C:17]1([NH:5][C:7]([C:8]2[CH2:16][CH2:6][N:5]([CH2:7][C:8]3[C:16]4[C:11](=[N:12][CH:13]=[CH:14][CH:15]=4)[NH:10][CH:9]=3)[CH2:4][CH:9]=2)=[O:2])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Product 1

HCID 9884048HCID 9884048, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the preceding hydrochloride in water was basified with aqueous sodium hydroxide and the resulting suspension extracted with dichloromethane (3×25 ml). The extracts were dried (MgSO4), evaporated and the residual gum (2.16 g) was combined with 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (1.75 g, 10 mmol) in xylene (50 ml) and the mixture stirred at reflux for 3.5 h. After decanting the mixture whilst hot, the supernatant was allowed to cool and the solid deposited collected and recrystallised twice from ethanol to leave the title compound as buff plates (0.21 g), m.p. 217°-220°; (Found C, 72.09; H, 5.98; N, 16.59. C20H20N4O requires C, 72.27; H, 6.06; N, 16.86%); δH (DMSO-d6) 2.36 (2H, br s, tetrahydropyridinyl CH2), 2.59 (2H, t, J 5.6 Hz, tetrahydropyridinyl CH2), 3.11 (2H, br s, tetrahydropyridinyl CH2), 3.75 (2H, s, ArCH2N), 6.60 (1H, br s, CR=CH), 7.00-7.06 (2H, m, ArH & 5-H), 7.28 (2H, t, J 8.3 Hz, ArH), 7.39 (1H, d, J 2.3 Hz, 2-H), 7.64 (2H, dd, J 8.6, 1.0 Hz, ArH), 8.03 (1H, dd, J 7.8, 1.2 Hz, 4-H), 8.20 (1H, dd, J 4.6, 1.5 Hz, 6-H), 9.60 (1H, s, NH), and 11.47 (1H, br s, 1-H); M/z (CI+, NH3) 333 (M+1)+.

Workup

  1. extractionthe resulting suspension extracted with dichloromethane (3×25 ml)
  2. dry with materialThe extracts were dried (MgSO4)
  3. customevaporated
  4. temperatureat reflux for 3.5 h
  5. customAfter decanting the mixture whilst hot, the supernatant
  6. temperatureto cool
  7. customthe solid deposited collected
  8. customrecrystallised twice from ethanol

Sources & evidence

ORD record
ord-b179578d0df342afb3dd3c6cc899b16c
Source dataset
uspto-grants-1996_10
Patent number
US05563152

Reaction notes

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