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Acetic Acid → (5-{[6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamino]methyl}-pyrimidin-2-yl)-methyl-amine

HRID 509983
Notes
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Reaction equation

HRID 509983 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[NH:12][CH:11]=1.[CH3:20][NH:21][C:22]1[N:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][N:23]=1.C(O)(=O)C.C([BH3-])#N>C(O)C>[F:1][C:2]1[N:7]=[C:6]([NH:8][CH2:28][C:25]2[CH:24]=[N:23][C:22]([NH:21][CH3:20])=[N:27][CH:26]=2)[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[NH:12][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 31609752-(Methylamino)pyrimidine-5-carbaldehydeHCID 582592126-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine

Product 1

HCID 67201595(5-{[6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamino]methyl}-pyrimidin-2-yl)-methyl-amine

Reagents, catalysts & solvents

1
HCID 702EthanolSolvent

Procedure

In a 2 mL microwave vial, 6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (137, 9.72 mg, 0.04 mmol) and 2-methylamino-pyrimidine-5-carbaldehyde (138, 11.0 mg, 0.08 mmol) were dissolved in 600 μL of 95:5 ethanol:acetic acid, and silica supported cyanoborohydride (50 mg, 1 mmol/g, 0.05 mmol) was added. The reaction was irradiated for 10 minutes at 160° C. in a microwave. The vial was centrifuged to condense the silica and the supernatant was removed by pipette into another vial. The residual silica was rinsed with 500 μL of ethanol, centrifuged and the supernatant added to the first supernatant. The solvents were removed under vacuum and the resulting material dissolved in 400 μL of dimethyl sulfoxide for purification by HPLC. Samples were purified on Phenomenex C18 column (50 mm×10 mm ID) with mobile phase A of 0.1% trifluoroacetic acid in water, mobile phase B of 0.1% trifluoroacetic acid in acetonitrile, 20-100% B over 16 minutes at a flow rate of 6 mL/min. Appropriate fractions were collected and solvents removed under vacuum to provide the desired compound. MS (ESI) [M+H+]+=378.3.

Workup

  1. additionwas added
  2. customThe reaction was irradiated for 10 minutes at 160° C. in a microwave
  3. customThe vial was centrifuged to condense the silica
  4. customthe supernatant was removed by pipette into another vial
  5. washThe residual silica was rinsed with 500 μL of ethanol
  6. additioncentrifuged and the supernatant added to the first supernatant
  7. customThe solvents were removed under vacuum
  8. dissolutionthe resulting material dissolved in 400 μL of dimethyl sulfoxide for purification by HPLC
  9. customSamples were purified on Phenomenex C18 column (50 mm×10 mm ID) with mobile phase A of 0.1% trifluoroacetic acid in water, mobile phase B of 0.1% trifluoroacetic acid in acetonitrile, 20-100% B over 16 minutes at a flow rate of 6 mL/min
  10. customAppropriate fractions were collected
  11. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-8ec53f5a2664403ca049fcb19dd37308
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096593B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes