Dichloromethane → HCID 118037375, compound

HRID 1508957Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[N:14]=[C:13]3[CH2:30][CH2:31][CH2:32][C:12]=23)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:41]>>[ClH:41].[N:17]1([C:15]2[N:14]=[C:13]3[CH2:30][CH2:31][CH2:32][C:12]3=[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][OH:1])=[CH:9][CH:8]=3)[CH:16]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 90338653HCID 90338653, compound

Product 1

HCID 118037375HCID 118037375, compoundYield 41%

Procedure

To a solution of tert-butyl 4-(4-((4-(2-hydroxyethyl)phenyl)amino)-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)piperazine-1-carboxylate (0.026 g, 0.059 mmol) in methylene chloride (5 mL) was added TFA (0.1 mL). The mixture stirred at rt for 16 h and purified by preparative HPLC (water/acetonitrile with 0.05% TFA), followed by formation of the hydrochloride salt to afford the title compound (0.010 g, 41%) as a yellow-brown solid. MW=411.37. 1H NMR (DMSO-d6, 500 MHz) δ 13.21 (s, 1H), 9.46-9.19 (m, 3H), 7.31 (d, J=8.0 Hz, 2H), 7.25 (d, J=8.0 Hz, 2H), 6.04 (s, 1H), 3.68-3.56 (m, 6H), 3.20 (br s, 4H), 3.05-2.96 (m, 2H), 2.81-2.72 (m, 4H), 2.19-2.10 (m, 2H); APCI MS m/z 339 [M+H]+.

Workup

custompurified by preparative HPLC (water/acetonitrile with 0.05% TFA)

Sources & evidence

ORD record: ord-568dbca8207e4a0db646c87bee3c9bae
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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