Hydroxyamine hydrochloride → HCID 9877758, compound

HRID 1582441Notes

Reaction equation

HRID 1582441 reaction equation
[CH:1]([C:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]2[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][C:4]=12)=O.Cl.[NH2:25]O>C(O)=O>[CH2:16]1[C:4]2=[C:3]([C:1]#[N:25])[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]2[CH2:12][CH2:13][NH:14][CH2:15]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22720322HCID 22720322, compound

Product 1

HCID 9877758HCID 9877758, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of tert-butyl 11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate in formic acid (1 mL) is treated with hydroxylamine hydrochloride (90 mg, 1.3 mmol) and heated to reflux. After 18 hrs, the reaction mixture is cooled to rt, quenched with 1M sodium hydroxide (15 mL), and extracted twice with ethyl acetate (20 mL). The combined organics are washed once with brine (20 mL), dried over MgSO4, filtered, and concentrated to give 224 mg of a crude solid. This material is purified by LC (230-400) silica gel eluting with 5% methanol/dichloromethane to afford 123 mg of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbonitrile as a red solid, mp 161-164° C. IR (drift) 3313, 2935, 2906, 2203, 1539, 1463, 1421, 1351, 1328, 1272, 1208, 1185, 822, 769, 752 cm−1.

Workup

  1. temperatureheated to reflux
  2. customquenched with 1M sodium hydroxide (15 mL)
  3. extractionextracted twice with ethyl acetate (20 mL)
  4. washThe combined organics are washed once with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 224 mg of a crude solid
  9. customThis material is purified by LC (230-400) silica gel eluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-08ec5e74b23e480a94ca21b23c06933e
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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