Trifluoroacetic acid methylene chloride → N,N-Dimethyl-3-(4-piperidinyl)-1H-pyrrolo[3,2-c]pyridin-6-amine

HRID 966119Notes

Reaction equation

HRID 966119 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[CH:19]=[N:20][C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:17]=3[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH3:24][N:23]([CH3:25])[C:21]1[N:20]=[CH:19][C:18]2[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:15][NH:16][C:17]=2[CH:22]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 69184354HCID 69184354, compound

Product 1

HCID 22312005N,N-Dimethyl-3-(4-piperidinyl)-1H-pyrrolo[3,2-c]pyridin-6-amineYield 100.7%

Procedure

The 4-(6-dimethylamino-1H-pyrrolo[3,2-c]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (135 mg, 0.39 mmol) was set stirring in 1:1 TFA/CH2Cl2. After 45 min the mixture was evaporated. The residue was dissolved in MeOH (10 mL) and neutralized with DOWEX 550A OH anion exchange resin to pH 8. The resin was then filtered off and MeOH was removed under reduced pressure to give 96 mg (100%) of a yellow solid. MS (electrospray): exact mass calculated for C14H20N4, 244.17; m/z found, 245.2 [M++H]. 1H NMR (CDCl3, 400 MHz): 9.23 (br s, 1H), 8.54 (s, 1H), 6.67 (s, 1H), 6.31 (d, J=0.98 Hz, 1H), 3.15 (d, J=2.13 Hz, 2H), 3.02 (s, 6H), 2.91-2.81 (m, 1H), 2.81-2.72 (m, 2H), 2.01 (d, J=12.52 Hz, 2H), 1.69-1.52 (m, 2H).

Workup

  1. customAfter 45 min the mixture was evaporated
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. filtrationThe resin was then filtered off
  4. customMeOH was removed under reduced pressure

Sources & evidence

ORD record
ord-f5065572b9664cbf9d747124ae786cec
Source dataset
uspto-grants-2005_10
Patent number
US06951851B2

Reaction notes

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