Triethylamine → HCID 66679189, compound

HRID 1626631Notes

Reaction equation

HRID 1626631 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:16]3[CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][C:8]=1[F:29])=[O:5])[CH3:2].C(N(CC)CC)C.[C:37]([N:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1)(=[O:39])[CH3:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:37]([N:40]1[CH2:45][CH2:44][CH:43]([N:20]2[CH2:21][C:16]3[C:15]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]4[CH3:28])=[N:14][C:13]([C:10]4[CH:11]=[CH:12][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[C:8]([F:29])[CH:9]=4)=[N:18][C:17]=3[CH2:19]2)[CH2:42][CH2:41]1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122563N-Acetyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 66678769HCID 66678769, compound2×

Product 1

HCID 66679189HCID 66679189, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-1-ethyl-3-(2-fluoro-4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (intermediate 18) (100 mg, 0.23 mmol) and triethylamine (64 μL, 0.46 mmol) in dry THF (3 ml) was added 1-acetylpiperidin-4-one (56 μL, 0.46 mmol) and stirred at room temperature for 30 min. To this sodium triacetoxyborohydride (97 mg, 0.46 mmol) was added. The reaction mixture was stirred at room temperature until analysis by LCMS indicated reaction was complete. The solvent was then removed in vacuo. Crude reaction mixture then was partitioned between ethyl acetate and water. The organic layer was recovered, dried with sodium sulphate and solvent removed in vacuo. Residue was then purified by prep HPLC (low pH) to afford a white solid (6.7 mg, 0.013 mmol, 6%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature until analysis by LCMS
  2. customreaction
  3. customThe solvent was then removed in vacuo
  4. customCrude reaction mixture
  5. customthen was partitioned between ethyl acetate and water
  6. customThe organic layer was recovered
  7. dry with materialdried with sodium sulphate and solvent
  8. customremoved in vacuo
  9. customResidue was then purified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-7c85b0a735624b9d94e393bcaeb2051f
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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