Hydrochloric Acid → HCID 49869073, compound

HRID 474901Notes

Reaction equation

HRID 474901 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[CH:24]=[C:23]4[C:19]([C:20]5[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][C:21]=5[N:22]4[CH3:25])=[CH:18][CH:17]=3)[C:12](=[O:38])[CH:11]=2)=[N:6][CH:7]=1.C[OH:40].[CH2:41]([Cl:43])[Cl:42].Cl>C(OCC)C>[CH2:41]([Cl:43])[Cl:42].[CH3:8][OH:9].[NH4+:6].[OH-:40].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[CH:24]=[C:23]4[C:19]([C:20]5[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][C:21]=5[N:22]4[CH3:25])=[CH:18][CH:17]=3)[C:12](=[O:38])[CH:11]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 58093403HCID 58093403, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 49869073HCID 49869073, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl 8-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-10-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indole-2(1H)-carboxylate (0.12 mg, 0.23 mmol) in 4:1 MeOH/CH2Cl2 (5.0 mL) was treated with anhydrous 1.0 M HCl in diethyl ether (46 mL), and the resulting solution was stirred at ambient temperature for 2 h. The solids were collected by filtration, washed with Et2O and dried. Preparative TLC (Analtech, 20×20 cm, 1000 microns, 80:18:2 CH2Cl2/MeOH/NH4OH) afforded the title compound (41 mg, 43%) as an off-white powder: 1H NMR (500 MHz, DMSO-d6) δ 8.61 (d, J=2.5 Hz, 1H), 7.84-7.80 (m, 1H), 7.66-7.64 (m, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.46 (d, J=8.5 Hz, 1H), 7.34 (s, 1H), 6.87 (dd, J=8.5, 1.5 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.95 (d, J=3.0 Hz, 1H), 5.21 (s, 2H), 4.0 (s, 2H), 3.64 (s, 3H), 3.06 (t, J=5.5 Hz, 2H), 2.83 (t, J=5.5 Hz, 2H), 1.77-1.76 (m, 2H); ESI MS m/z 419 [M+H]+.

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with Et2O
  3. customdried

Sources & evidence

ORD record
ord-165e2178d0eb4924913b77148295e79b
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…