Acetic Acid → HCID 71622962, compound

HRID 1479068Notes

Reaction equation

HRID 1479068 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)=O.[Cl:18][C:19]1[C:27]([CH3:28])=[N:26][C:25]2[N:21]([N:22]=[C:23]3[CH2:31][N:30]([C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH2:41][CH:42]4[CH2:46][CH2:45][NH:44][CH2:43]4)=[O:33])[CH2:29][C:24]3=2)[C:20]=1[CH3:47].[CH3:48][C:49]([CH3:51])=O.CC(O)=O>C(Cl)Cl>[Cl:18][C:19]1[C:27]([CH3:28])=[N:26][C:25]2[N:21]([N:22]=[C:23]3[CH2:31][N:30]([C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH2:41][CH:42]4[CH2:46][CH2:45][N:44]([CH:49]([CH3:51])[CH3:48])[CH2:43]4)=[O:33])[CH2:29][C:24]3=2)[C:20]=1[CH3:47]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 131736547HCID 131736547, compound

Product 1

HCID 71622962HCID 71622962, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (90 mg; 0.42 mmol; 4 eq.) was added to a solution of (6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-[2-(pyrrolidin-3-ylmethoxy)-phenyl]-methanone formic acid salt (50 mg; 0.11 mmol; 1 eq.), acetone (47 μL; 0.64 mmol; 6 eq.) and AcOH (7 μL; 0.13 mmol; 1.2 eq.) in DCM (3 mL) and the reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with DCM, washed with sat. aq. NaHCO3, dried over sodium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (47 mg, 76%) as a white solid. 1H NMR (CDCl3) δ 7.44-7.30 (m, 2H), 7.12-6.98 (m, 1H), 6.98-6.87 (m, 1H), 5.07-4.92 (m, 2H), 4.63 (br s, 2H), 4.09-3.86 (m, 2H), 2.88 (d, J=18.2 Hz, 4H), 2.65 (d, J=23.0 Hz, 5H), 2.50-2.05 (m, 3H), 2.04-1.84 (m, 1H), 1.58 (dt, J=13.2, 5.8 Hz, 1H), 1.02-0.81 (m, 6H). HPLC (max plot) 94.3%, Rt 2.92 min. UPLC/MS: (MS+) 468.5 ([M+H]+).

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by mass

Sources & evidence

ORD record
ord-43ef34fc0bea42cf8675b1871f37cc03
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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