HCID 178448314, compound → HCID 178448885, compound

HRID 243368Notes

Reaction equation

HRID 243368 reaction equation
[CH3:1][CH:2]([CH3:30])[C@H:3]([NH:20][C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2)[C:4]([NH:6][C:7]1[C:8]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][CH:12]=1)=O>CC(O)=O>[CH3:1][CH:2]([CH3:30])[CH:3]([NH:20][C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2)[C:4]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1

Participants

3

Reactant 1

HCID 178448314HCID 178448314, compound

Product 1

HCID 178448885HCID 178448885, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (S)-3-methyl-N-(2-phenylaminopyridin-3-yl)-2-(9H-purin-6-ylamino)butyramide (821 mg, 2.0 mmol) in AcOH (10 mL) was heated at 100° C. for 2 h. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with DCM and the combined organic fractions dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 196 as a light brown solid (365 mg, 46%). LCMS (Method K): RT 3.18 min [M+H]+ 385.1. 1H NMR (DMSO-d6, 400 MHz): δ 8.29-7.99 (4H, m), 7.78-7.42 (6H, m), 7.31 (1H, dd, J=8.01, 4.75 Hz), 5.40 (1H, br s), 2.45-2.34 (1H, m), 0.95 (3H, d, J=6.69 Hz), 0.81 (3H, br d, J=6.59 Hz). Signals split due to presence of rotamers/tautomers

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe resulting residue partitioned between DCM
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialthe combined organic fractions dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-06b3e0a0cc634323932742289c9f1bfe
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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