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

HRID 474978Notes

Reaction equation

HRID 474978 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:18]=[CH:19][C:20]4[C:29]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][C:23]=5[N:22]([CH3:37])[C:21]=4[N:38]=3)[C:13](=[O:39])[CH:12]=2)=[N:7][CH:8]=1>CO.CCOCC>[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:18]=[CH:19][C:20]4[C:29]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24][C:23]=5[N:22]([CH3:37])[C:21]=4[N:38]=3)[C:13](=[O:39])[CH:12]=2)=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58093352tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

Product 1

HCID 668736214((5-Fluoropyridin-2-yl)methoxy)-1-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)pyridin-2(1H)-one hydrochlorideYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.25 M HCl in MeOH (6.0 mL) was added to tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (0.12 g, 0.22 mmol) and the resulting solution was stirred under N2 at ambient temperature for 20 h. The resulting suspension was diluted with Et2O (30 mL), and the resulting solids were collected by filtration to provide the title compound (92 mg, 92%) as an off-white solid: mp 238-240° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.43 (s, 2H), 8.62 (d, J=2.0 Hz, 1H), 8.02 (d, J=8.5 Hz, 1H), 7.84-7.80 (m, 2H), 7.67-7.64 (m, 1H), 7.30 (d, J=8.5 Hz, 1H), 6.19 (dd, J=7.5, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.23 (s, 2H), 3.73 (s, 3H), 3.40-3.37 (m, 2H), 3.34-3.30 (m, 4H), 3.18-3.14 (m, 2H); ESI MS m/z 420 [M+H]−; HPLC (Method A) 98.8% (AUC), tR=13.5 min.

Workup

  1. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-0d31e523ae0c476c97a9139511202012
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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