Cyclopentylamine → HCID 58154550, compound

HRID 2359414Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([C:31]([OH:33])=O)[CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:34]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH:34]1([NH:39][C:31]([C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[C:23]=2[N:22]=[C:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:16]=2)[CH:30]=[CH:29]3)=[O:33])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 66884154HCID 66884154, compound

Product 1

HCID 58154550HCID 58154550, compound

Procedure

The same general amide coupling procedure outlined above was employed using 2-(3-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)phenyl)quinoline-8-carboxylic acid and cyclopentylamine. Purification by column chromatography (1:5 ethyl acetate/pentane), followed by treatment with 4N HCl/MeOH and concentration produced the product as a yellow solid. MS (ESI) calcd for C26H29N3O2 (m/z): 415.23. found: 416 [M+1].

Workup

customPurification by column chromatography (1:5 ethyl acetate/pentane)
concentrationfollowed by treatment with 4N HCl/MeOH and concentration

Sources & evidence

ORD record: ord-a0fd4cb07fd742afaa408aec0f664496
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685970B2

Reaction notes

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