Hydrochloric Acid → HCID 66873162, compound

HRID 474902Notes

Reaction equation

HRID 474902 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]5[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][C:22]=5[N:23]4[CH3:26])=[CH:19][CH:18]=3)[C:13](=[O:32])[CH:12]=2)=[N:7][CH:8]=1>CO>[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]5[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][C:22]=5[N:23]4[CH3:26])=[CH:19][CH:18]=3)[C:13](=[O:32])[CH:12]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49869073HCID 49869073, compound

Product 1

HCID 66873162HCID 66873162, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.25 M HCl in MeOH (75 μL, 0.094 mmol) was added to a solution of 4-((5-fluoropyridin-2-yl)methoxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin 2(1H)-one (39 mg, 0.094 mmol) in MeOH (2.0 mL), and the resulting solution was stirred at ambient temperature for 1 h. The mixture was concentrated to dryness under reduced pressure to yield the title compound (36 mg, 85%) as a light yellow powder: mp 268-275° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.62 (d, J=3.0 Hz, 1H), 8.19 (br s, 1H), 7.84-7.80 (m, 1H), 7.66-7.64 (m, 1H), 7.58-7.51 (m, 2H), 7.45 (d, J=1.5 Hz, 1H), 6.95 (dd, J=8.0, 3.0 Hz, 1H), 6.12 (dd, J=7.5, 2.5 Hz, 1H), 5.96 (d, J=3.0 Hz, 1H), 5.21 (s, 2H), 4.39 (s, 2H), 3.71 (s, 3H), 3.38-3.36 (m, 2H), 2.95-2.93 (m, 2H), 1.93-1.92 (m, 2H); ESI MS m/z 419 [M+H]+; HPLC (Method A) 98.3% (AUC), tR=13.0 min.

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-57ac42a4a7834c8cb4b85a89d4b5d9c9
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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