Ammonium Chloride → HCID 68283901, compound

HRID 1469463Notes

Reaction equation

[N:1]([C:4]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([CH3:21])[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[C:8]2[CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][C:7]1=2)=[N+]=[N-].[Cl-].[NH4+]>CCO.O.[Zn]>[CH3:20][N:17]1[CH2:18][CH2:19][C:7]2[N:6]([CH2:5][C:4]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)([NH2:1])[CH3:21])[C:14]3[CH:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=3[C:8]=2[CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

5-(2-Azido-2-(pyridin-3-yl)propyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (Crude) (500 mg, 1.4 mmol) was dissolved in EtOH (4 mL) and water (1 mL). Ammonium chloride (243 mg, 4.5 mmol) followed by zinc dust (293 mg, 4.5 mmol) were added to the reaction mixture and heated at 80° C. for 1 h. The reaction mixture was concentrated to dryness, basified with aqueous ammonia solution and extracted with EtOAc (150 mL). The organic layer was dried over sodium sulfate, evaporated in vacuo and purified by reverse phase HPLC to afford 2 mg of 1-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-3-yl)propan-2-amine. 1H NMR (CD3OD, freebase): δ (ppm): 8.39 s (1H), 8.3 d (1H), 7.72 d (1H), 7.32 t (1H), 7.11 (1H), 6.91 d (1H), 6.8 d (1H), 4.18 dd (2H), 3.61 dd (2H), 2.7 m (2H), 2.46 s (3H), 2.35 s (3H), 2.26 m (2H). Chiral HPLC provided enantiomers 149a and 149b.

Workup

additionwere added to the reaction mixture
concentrationThe reaction mixture was concentrated to dryness
extractionextracted with EtOAc (150 mL)
dry with materialThe organic layer was dried over sodium sulfate
customevaporated in vacuo
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-4217c61de7ff4a39bf7f81aad9a248dd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006263B2

Reaction notes

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