Dimethylformamide → HCID 59558475, compound

HRID 1175124Notes

Reaction equation

HRID 1175124 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2].[O:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[Li].C(OC(N[CH:34]([CH:40]1[CH2:42][CH2:41]1)OS(C)(=O)=O)=O)(C)(C)C.C[N:44]([CH:46]=[O:47])C>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:41][C:42]2([NH:44][C:46]([O:20][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:47])[CH2:34][CH2:40]2)[N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 59558516HCID 59558516, compoundHCID 87105556HCID 87105556, compoundHCID 178506942HCID 178506942, compound

Product 1

HCID 59558475HCID 59558475, compound

Conditions

Temperature
100 °C

Procedure

8-Chloro-4,5-dihydro-2H-1,2,7-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester (239 mg; 0.9 mmol) in DMF (4 ml) is treated at 50 C with LiOtBu (1N in THF; 0.9 ml; 0.9 mmol) for 10 minutes. (1-tert.-Butoxycarbonylamino-1-methanesulfonyloxymethyl)-cyclo-propane (U.S. Pat. No. 4,622,418) (250 mg; 0.9 mmol) in DMF (1 ml) is added and the mixture heated to 100° C. for 30 minutes. The reaction mixture is evaporated to dryness, taken up in TBME and washed several times with 0.5 N NaOH. The organic phase is dried over Na2SO4 and evaporated to dryness to yield the title compound as yellow crystals. 1H-NMR (400 MHz; DMSO-d6): 8.37 (s, 1H); 7.62 (s, 1H); 7.04 (s, 1H); 4.69 (s, 2H); 4.33 (q, 2H); 3.02 (m, 2H); 2.95 (m, 2H); 1.37 (t, 3H); 1.35 (s, 9H); 0.93 (m, 2H); 0.65 (m, 2H). MS (m/z) ES+: 447 (MH+).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. washwashed several times with 0.5 N NaOH
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a5b53515dce84a4689c7939caf24cdea
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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