Hydrazine hydrate (1:1) → HCID 70007339, compound

HRID 1266037Notes

Reaction equation

HRID 1266037 reaction equation
O.[NH2:2]N.C[N:5](C)/[CH:6]=[CH:7]/[C:8]([C:10]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:17][C:16]2[CH2:26][NH:27][CH2:28][C:29](=[O:30])[N:14]3[C:15]=2[C:11]=1[CH:12]=[CH:13]3)=O>C1COCC1>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[C:10]([C:8]3[NH:2][N:5]=[CH:6][CH:7]=3)=[C:11]3[C:15]4=[C:16]([CH2:26][NH:27][CH2:28][C:29](=[O:30])[N:14]4[CH:13]=[CH:12]3)[CH:17]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86758925HCID 86758925, compound

Product 1

HCID 70007339HCID 70007339, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrazine monohydrate (5.14 mmol, 0.26 mL) was added to a solution of 7-[(E)-3-Dimethylamino-allanoyl]-6-(4-fluoro-phenyl)-3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 159) (0.257 mmol, 0.097 g) in 10 mL THF at rt. The reaction mixture was stirred for 42 h. The reaction mixture was evaporated to dryness. The residue was taken up in 2N HCl and extracted with EtOAc several times. The combined organic layers was dried over anhydrous MgSO4 and concentrated to give a yellow oil which was purified by flash silica gel chromatography eluting with a gradient of 0-3% MeOH in CHCl3 to give 0.020 g (23%) of a yellow solid: mp=173-175° C.; 1H NMR (DMSO-d6) δ 3.45-3.52 (m, 2H), 4.03-4.08 (m, 2H), 5.64 (br s, 1H), 7.23 (t, 1H, J=6.0 Hz), 7.32 (t, 2H, J=9.0 Hz), 7.38-7.55 (m, 3), 7.88 (d, 1H, J=6.0 Hz), 8.36-8.43 (m, 2H), 12.67 (br s, 1H); HRMS calcd. for C20H15N4OF (M+) 346.1221, found (M+) 346.1225; Anal. for (C20H15N4OF.1.0MeOH) C, H, N.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionextracted with EtOAc several times
  3. dry with materialThe combined organic layers was dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customto give a yellow oil which
  6. customwas purified by flash silica gel chromatography
  7. washeluting with a gradient of 0-3% MeOH in CHCl3

Sources & evidence

ORD record
ord-18c4da1eae254e3a9554f2fb3c05c349
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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