Hydroxyamine hydrochloride → HCID 86758921, compound

HRID 1266029Notes

Reaction equation

HRID 1266029 reaction equation
Cl.[NH2:2][OH:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([CH:25]=O)=[C:13]3[C:17]4=[C:18]([CH2:20][NH:21][CH2:22][C:23](=[O:24])[N:16]4[CH:15]=[CH:14]3)[CH:19]=2)=[CH:7][CH:6]=1>N1C=CC=CC=1>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([CH:25]=[N:2][OH:3])=[C:13]3[C:17]4=[C:18]([CH2:20][NH:21][CH2:22][C:23](=[O:24])[N:16]4[CH:15]=[CH:14]3)[CH:19]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86758922HCID 86758922, compound

Product 1

HCID 86758921HCID 86758921, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydroxylamine hydrochloride (0.10 g, 0.325 mmol) was added to a solution of 6-(4-fluoro-phenyl)-1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-7-carbaldehyde (56.0 mg, 0.813 mmol) in pyridine (10 mL) and stirred at rt for 20 h. Upon consumption of the aldehyde as indicated by TLC, the solvent was removed in vacuo. The residue was taken up in 2N HCl and extracted with EtOAc several times. The combined organic extracts were dried over anhydrous MgSO4 and concentrated to give 97 mg (92%) of a pale-yellow solid: mp 277-279° C.; 1H NMR (DMSO-d6) δ 3.50 (br s, 2H), 4.12-4.14 (m, 2H), 7.30 (t, 1H, J=6.0 Hz), 7.43 (t, 2H, J=9.0 Hz), 7.57-7.62 (m, 2H), 7.89 (s, 1H), 7.94 (d, 1H, J=9.0 Hz), 8.33 (d, 1H, J=6.0 Hz), 8.41 (t, 1H, J=6.0 Hz), 10.80 (s, 1H). HRMS calcd. for C18H14N3O2F 323.1070 (M+), found 323.1066.

Workup

  1. customUpon consumption of the aldehyde
  2. customthe solvent was removed in vacuo
  3. extractionextracted with EtOAc several times
  4. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a309f3079c4443c0a76296ecc1437e8c
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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