Dimethylformamide dimethyl acetal → HCID 59161321, compound

HRID 545569Notes

Reaction equation

HRID 545569 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1)[C:12]1[CH2:11][CH2:10][C@@H:9]([NH:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[CH2:8][C:7]2=1)(=[O:3])[CH3:2].CO[CH:33](OC)[N:34](C)C.Cl.NO>O1CCOCC1.O>[F:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:13]1[C:12]2[CH2:11][CH2:10][C@@H:9]([NH:25][C:26](=[O:30])[CH:27]([CH3:28])[CH3:29])[CH2:8][C:7]=2[C:6]2[C:14]1=[CH:15][CH:16]=[C:4]([C:1]1[O:3][N:34]=[CH:33][CH:2]=1)[CH:5]=2

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 443297Hydroxyamine hydrochlorideHCID 59161296HCID 59161296, compound

Product 1

HCID 59161321HCID 59161321, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

Combine (R)-N-[6-Acetyl-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 191) (0.055 g, 0.14 mmol) and dimethylformamide dimethylacetal (0.81 g, 6.8 mmol) and heat at 100° C. for 82 h. Concentrate in vacuo and treat the resulting residue with hydroxylamine hydrochloride (0.012 g, 0.18 mmol) in dioxane at 23° C. for 1 h before warming to 40° C. briefly. Dilute with water and collect 0.029 g of a solid by filtration. Recrystallize from EtOAc/hexanes to yield a light yellow solid. mp: 238-241° C.; MS (ES): m/z 432 (M+1); HPLC: Rt=2.59 (85%).

Workup

  1. concentrationConcentrate in vacuo
  2. customcollect 0.029 g of a solid
  3. filtrationby filtration
  4. customRecrystallize from EtOAc/hexanes
  5. customto yield a light yellow solid

Sources & evidence

ORD record
ord-bb2c8c6c5d4948dba87d45b1c8d9c37f
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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