Hydrochloric Acid → HCID 66679210, compound

HRID 1626647Notes

Reaction equation

HRID 1626647 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.Cl.C(N(CC)CC)C.O=[CH:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][N:21]([CH2:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])[CH2:20][C:18]=4[N:19]=3)=[CH:12][CH:13]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11124-Oxobutanoic acidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 46894114(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

Product 1

HCID 66679210HCID 66679210, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (Example 3) as a HCl salt (100 mg, 0.23 mmol) and triethyamine (64 μL, 0.46 mmol) in DCE (3 mL, anhydrous), and DMF 0.5 mL, anhydrous) was added 4-oxobutanoic acid (45 μL, 0.46 mmol). Reaction mixture was stirred at room temperature for 30 mins. 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. Solvent was then removed in vacuo. Purified by prep. HPLC (high pH) to afford a white solid (4.2 mg, 0.008 mmol, 4%).

Workup

  1. customReaction mixture
  2. stirringThe reaction mixture was stirred at room temperature until analysis by LCMS
  3. customreaction
  4. customSolvent was then removed in vacuo
  5. customPurified by prep

Sources & evidence

ORD record
ord-38d061e81e9f45f888769203897a3df5
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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