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

HRID 474980노트

반응식

HRID 474980 반응식
[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:12]=[N:13][N:14]([C:18]3[CH:19]=[CH:20][C:21]4[C:30]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25][C:24]=5[N:23]([CH3:38])[C:22]=4[N:39]=3)[C:15](=[O:17])[CH:16]=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:12]=[N:13][N:14]([C:18]3[CH:19]=[CH:20][C:21]4[C:30]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][C:24]=5[N:23]([CH3:38])[C:22]=4[N:39]=3)[C:15](=[O:17])[CH:16]=2)=[N:7][CH:8]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric Acid2회HCID 58093420tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-6-oxopyridazin-1(6H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

생성물 1

HCID 668741695-((5-Fluoropyridin-2-yl)methoxy)-2-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)pyridazin-3(2H)-one hydrochloride수율 73%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 3283Diethyl Ether용매

실험 절차

1.25 M HCl in MeOH (4.0 mL) was added to tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-6-oxopyridazin-1(6H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (55 mg, 0.11 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. Additional 1.25 M HCl in MeOH (2.0 mL) was added, and the resulting solution was stirred at ambient temperature for 24 h. The resulting solution was diluted with Et2O (30 mL), and the resulting solids were collected by filtration to provide the title compound (35 mg, 73%) as an off-white powder: mp 226-230° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.12 (s, 2H), 8.64 (d, J=3.0 Hz, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.98 (d, J=2.5 Hz, 1H), 7.85 (ddd, J=11.5, 8.5, 2.5 Hz, 1H), 7.72-7.69 (m, 1H), 7.15 (d, J=8.5 Hz, 1H), 6.51 (d, J=3.0 Hz, 1H), 5.30 (s, 2H), 3.71 (s, 3H), 3.45-3.39 (m, 2H), 3.38-3.31 (m, 2H), 3.30-3.28 (m, 2H), 3.15-3.14 (m, 2H); ESI MS m/z 421 [M+H]+; HPLC (Method A) 98.8% (AUC), tR=11.6 min.

후처리

  1. stirringthe resulting solution was stirred at ambient temperature for 24 h
  2. filtrationthe resulting solids were collected by filtration

출처 및 근거

ORD 기록
ord-09e40487e81641f193d9c4aaea2f354b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637501B2

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