Dimethylformamide → HCID 86758916, compound

HRID 1266016Notes

Reaction equation

HRID 1266016 reaction equation
O=P(Cl)(Cl)Cl.[C:6]1(=[O:19])[N:17]2[C:18]3[C:14]([CH:15]=[CH:16]2)=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][NH:8][CH2:7]1.CN([CH:23]=[O:24])C>>[O:19]=[C:6]1[N:17]2[C:18]3[C:14]([CH:15]=[CH:16]2)=[C:13]([CH:23]=[O:24])[CH:12]=[CH:11][C:10]=3[CH2:9][NH:8][CH2:7]1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 69701319HCID 69701319, compound

Product 1

HCID 86758916HCID 86758916, compoundYield 95%

Procedure

POCl3 (16.37 g, 106.76 mmol) was slowly added to DMF (225 mL) at 0° C. The mixture was stirred for 15 minutes and then treated with a solution of 3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 42, 1.46 g, 7.85 mmol) in DMF (10 mL). The reaction mixture was warmed to rt and stirred for 17 h. After removing all solvent, the residue was taken up in H2O, made basic (pH 12-14) using 50% aqueous NaOH and extracted with EtOAc several times. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give 1.6 g (95%) of a pale-yellow solid: 1H NMR (DMSO-d6) δ 3.58-3.61 (m, 2H), 4.48 (bs, 2H), 7.37 (t, 1H, J=7.5 Hz), 7.97 (d, 1H, J=7.5 Hz), 8.33-8.35 (m, 2H), 8.43-8.45 (m, 1H), 9.95 (s, 1H). HRMS calcd. for C12H10N2O2 (M+) 214.0742, found 214.0737. Anal. (Cl2H10N2O2.0.1H2O) C, H, N.

Workup

  1. stirringstirred for 17 h
  2. customAfter removing all solvent
  3. extractionextracted with EtOAc several times
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1aac5d06c504892ae5b6e04853418a1
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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