Hydrochloric Acid → 4-((5-Fluoropyridin-2-yl)methoxy)-1-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[3,2-c]azepin-2-yl)pyridin-2(1H)-one hydrochloride

HRID 474992Notes

Reaction equation

HRID 474992 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:17]=[CH:18][C:19]4[C:23]5[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH2:27][CH2:28][C:22]=5[N:21]([CH3:36])[C:20]=4[N:37]=3)[C:12](=[O:38])[CH:11]=2)=[N:6][CH:7]=1.[ClH:39]>CO>[ClH:39].[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:17]=[CH:18][C:19]4[C:23]5[CH2:24][NH:25][CH2:26][CH2:27][CH2:28][C:22]=5[N:21]([CH3:36])[C:20]=4[N:37]=3)[C:12](=[O:38])[CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66873230tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-10-methyl-7,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[3,2-c]azepine-6(5H)-carboxylate

Product 1

HCID 668735774-((5-Fluoropyridin-2-yl)methoxy)-1-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[3,2-c]azepin-2-yl)pyridin-2(1H)-one hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-10-methyl-7,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[3,2-c]azepine-6(5H)-carboxylate (130 mg, 0.250 mmol) in 1.25 M HCl in MeOH (4.0 mL) was stirred at ambient temperature for 72 h. The solution was concentrated and dried to provide the title compound (108 mg, 95%) as a brown-yellow powder: 1H NMR (500 MHz, DMSO-d6) δ 9.15 (s, 2H), 8.62 (d, J=3.0 Hz, 1H), 8.16 (d, J=8.5 Hz, 1H), 7.88-7.80 (m, 2H), 7.67-7.64 (m, 1H), 7.35 (d, J=8.0 Hz, 1H), 6.19 (dd, J=8.0, 2.5 Hz, 1H), 5.99 (d, J=2.5 Hz, 1H), 5.23 (s, 2H), 4.46 (s, 2H), 3.75 (s, 3H), 3.49-3.40 (m, 2H), 3.36-3.20 (m, 2H), 2.19-2.08 (m, 2H); ESI MS m/z 420 [M+H]+; HPLC (Method A) 98.2% (AUC), tR=12.2 min.

Workup

  1. concentrationThe solution was concentrated
  2. customdried

Sources & evidence

ORD record
ord-0beabddec39040658709df83475f7081
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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