Tetrahydrofuran → HCID 59161255, compound

HRID 545552Notes

Reaction equation

HRID 545552 reaction equation
[N+](C1C=CC(O[C:11](=[O:36])[NH:12][CH:13]2[CH2:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:26]#[N:27])[CH:22]=4)[N:17]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[C:16]=3[CH2:15][CH2:14]2)=CC=1)([O-])=O.Cl.CN.[CH2:40]([N:42](CC)CC)C.C1COCC1>O>[C:26]([C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1)[C:16]1[CH2:15][CH2:14][CH:13]([NH:12][C:11]([NH:42][CH3:40])=[O:36])[CH2:25][C:24]2=1)#[N:27]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 57431674HCID 57431674, compound

Product 1

HCID 59161255HCID 59161255, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine [6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-carbamic acid 4-nitrophenyl ester (Preparation 55) (306 mg, 0.63 mmol), methylamine hydrochloride (426 mg, 6.30 mmol), triethylamine (1.40 g, 1.93 mL, 13.9 mmol), and THF (30 mL). Stir the reaction mixture at room temperature for 18 h, then dilute with water (100 mL). Extract into EtOAc (3×65 mL), dry the combined organic portions (MgSO4), filter, and concentrate to give the crude product (310 mg) as a yellow oil. Purify the crude product on 40 g silica gel (50-100% (4% (2M NH3/MeOH)/CH2Cl2)/hexanes) to give 58 mg (24%) of the title compound as a yellow solid. MS (ES): m/z 377 (M+1); HPLC (Method B): Rt=3.22 min (98%).

Workup

  1. extractionExtract into EtOAc (3×65 mL)
  2. dry with materialdry the combined organic portions (MgSO4)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give the crude product (310 mg) as a yellow oil
  6. customPurify the crude product on 40 g silica gel (50-100% (4% (2M NH3/MeOH)/CH2Cl2)/hexanes)

Sources & evidence

ORD record
ord-d7e7c09724374dddbdeebb65b580d0e3
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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