Hydrochloric Acid → HCID 24900804, compound

HRID 421646Notes

Reaction equation

HRID 421646 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:14]=1.[OH-].[K+].Cl[CH2:21][C:22]1[NH:23][CH2:24][CH2:25][CH2:26][N:27]=1.Cl>CS(C)=O>[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:21][C:22]3[NH:27][CH2:26][CH2:25][CH2:24][N:23]=3)[C:6]=2[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 426329HCID 426329, compoundHCID 152709842-amino-9H-pyrido[2,3-b]indole-3-carboxamide

Product 1

HCID 24900804HCID 24900804, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of 2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 100 mg, 0.44 mmol) in dimethyl sulfoxide (1 mL) was added powdered potassium hydroxide (370 mg, 6.6 mmol), and the resulting mixture stirred at room temperature for 10 min. 2-(Chloromethyl)-1,4,5,6-tetrahydropyrimidine.HCl (Stillings, M. R., J. Med. Chem. 1986, 29, 2280-2284; 220 mg, 1.3 mmol) in dimethyl sulfoxide (1 mL) was added dropwise to the mixture over 0.5 h at 5-10° C. Upon completion of addition, the reaction was allowed to stir overnight at room temperature. The crude reaction mixture was concentrated under reduced pressure and purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN) to yield 2-amino-9-(1,4,5,6-tetrahydropyrimidin-2-ylmethyl)-9H-pyrido[2,3-b]indole-3-carboxamide (32, 14 mg, 10%). NH4OAc standard conditions. DAD Retention time=4.42 min. M+H=323. 1H NMR (300 MHz, MeOD): δ 8.73 (s, 1H), 8.49 (s, 1H), 7.94 (d, J=6.9 Hz, 1H), 7.42-7.40 (m, 2H), 7.33-7.27 (m, 1H), 5.29 (s, 2H), 3.45 (t, J=5.7 Hz, 4H), 2.04 (t, J=5.7 Hz, 2H).

Workup

  1. additionUpon completion of addition
  2. stirringto stir overnight at room temperature
  3. customThe crude reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. custompurified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN)

Sources & evidence

ORD record
ord-a52dd8b79bc942d08f078a91a7b5f0a1
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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