Trifluoroacetic acid → 1-(4-(6-Cyano-7-(piperidin-4-ylmethoxy)quinolin-4-yloxy)phenyl)-3-(thiazol-2-yl)urea

HRID 853591Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:36][C:37]5[S:38][CH:39]=[CH:40][N:41]=5)=[O:35])=[CH:29][CH:28]=4)=[CH:21][CH:22]=[N:23]3)=[CH:18][C:17]=2[C:42]#[N:43])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[C:42]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=1[O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[N:23]=[CH:22][CH:21]=[C:20]2[O:26][C:27]1[CH:28]=[CH:29][C:30]([NH:33][C:34]([NH:36][C:37]2[S:38][CH:39]=[CH:40][N:41]=2)=[O:35])=[CH:31][CH:32]=1)#[N:43]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 865914824-{6-Cyano-4-[4-(3-thiazol-2-ylureido)phenoxy]quinolin-7-yloxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 229363771-(4-(6-Cyano-7-(piperidin-4-ylmethoxy)quinolin-4-yloxy)phenyl)-3-(thiazol-2-yl)ureaYield 110%

Procedure

4-(6-Cyano-4-(4-(3-thiazol-2-yl-ureido)-phenoxy)-quinolin-7-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl-ester (240 mg) was deprotected with trifluoroacetic acid in the same manner as Production Example 670-4 to obtain the title compound (220 mg) as a solid.

Sources & evidence

ORD record: ord-b7f2f6877f7040b7928640f2ff69dc71
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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