Ammonia → HCID 44160181, compound

HRID 517862Notes

Reaction equation

HRID 517862 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13](OCC)=[O:14])[C:6]3[CH2:18][CH2:19][N:20]([CH3:22])[CH2:21][C:5]=3[C:4]=2[CH:3]=1.[NH3:23]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]([NH2:23])=[O:14])[C:6]3[CH2:18][CH2:19][N:20]([CH3:22])[CH2:21][C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 44159333Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate

Product 1

HCID 44160181HCID 44160181, compound

Procedure

Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate (0.1 g, 0.315 mmol) was taken in 4 ml aqueous ammonia and microwaved at 120° C. for 5 minutes. The solid product precipitated out after the reaction was filtered through Buchner funnel and washed with 10% sodium bicarbonate (10 ml×2) followed by demineralised water (10 ml×2) wash to obtain 1.25 mg of 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanamide as TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 ml). 1H NMR (DMSO) 9.85 (bs, 1H), 7.5-7.6 (m, 2H), 7.4 (s, 1H), 7.2 (d, 1H), 6.85 (s, 1H), 4.6-4.7 (m, 2H), 4.4 (t, 2H), 3.7-3.8 (m, 2H), 3.1-3.2 (m, 4H), 3.0 (s, 3H).

Workup

  1. custommicrowaved at 120° C. for 5 minutes
  2. customThe solid product precipitated out after the reaction
  3. filtrationwas filtered through Buchner funnel
  4. washwashed with 10% sodium bicarbonate (10 ml×2)
  5. washwash

Sources & evidence

ORD record
ord-ea902b5900ae4eada718a7c0e2138ca1
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

Loading…