Diethyl Ether → HCID 11489516, compound

HRID 751425Notes

Reaction equation

HRID 751425 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15]=2[CH:29]=[O:30])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(#N)C.CCOCC>ClCCl>[N:11]1([C:14]2[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15]=2[CH:29]=[O:30])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 6422Trifluoroacetic acid2×HCID 86596817HCID 86596817, compound

Product 1

HCID 11489516HCID 11489516, compoundYield 117.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-formyl-1-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (60 mg, 0.15 mmol) in dichloromethane (6 mL) is treated with trifluoroacetic acid (0.18 mL, 0.18 mmol). The resulting solution is allowed to stir at room temperature for 4 days to form a creamy suspension before treating the reaction with a further aliquot of trifluoroacetic acid (0.20 mL, 2.0 mmol) to give an orange solution. After stirring for a further 20 hours, the reaction mixture is evaporated to give an orange oil. Trituration of the crude product salt with acetonitrile and ether gives 54 mg of 2-piperazin-1-yl-1-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde; bis-trifluoro-acetic acid salt as a tan solid (68% yield). LC/MS: retention time 1.72 min, m/e 308 (M+H). 1H NMR (300 MHz, DMSO-d6): 10.16 (1H, s), 8.86 (1H, d), 8.78 (2H, br.s), 8.74 (1H, d), 8.41 (1H, d), 8.17-8.13 (2H, m), 7.70 (1H, dd), 7.30 (1H, dd), 3.50-3.46 (4H, m), 3.06-3.00 (4H, m).

Workup

  1. customto form a creamy suspension
  2. additionbefore treating
  3. customto give an orange solution
  4. stirringAfter stirring for a further 20 hours
  5. customthe reaction mixture is evaporated
  6. customto give an orange oil

Sources & evidence

ORD record
ord-844a575e6d2e4a6db5bb49a3aadbfee0
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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