Trifluoroacetic acid → N-(3-(2-Fluorobenzyl)-3-(methoxymethyl)piperidin-1-yl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

HRID 530888Notes

Reaction equation

[F:1][C:2]1[CH:55]=[CH:54][CH:53]=[CH:52][C:3]=1[CH2:4][C:5]1([CH2:49][O:50][CH3:51])[CH2:10][CH2:9][CH2:8][N:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:18]=[C:17]3[C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH3:48])[CH:43]=2)=[O:13])[CH2:6]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[F:1][C:2]1[CH:55]=[CH:54][CH:53]=[CH:52][C:3]=1[CH2:4][C:5]1([CH2:49][O:50][CH3:51])[CH2:10][CH2:9][CH2:8][N:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[C:17]3[C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH3:48])[CH:43]=2)=[O:13])[CH2:6]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 68074196N-(3-(2-Fluorobenzyl)-3-(methoxymethyl)piperidin-1-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 67985892N-(3-(2-Fluorobenzyl)-3-(methoxymethyl)piperidin-1-yl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

Procedure

In a flask, N-(3-(2-fluorobenzyl)-3-(methoxymethyl)piperidin-1-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide (crude, from previous step) was reacted with trifluoroacetic acid (3 mL) for 1 hour. After reaction completion triethylsilane (0.1 mL) was added, and the reaction was stirred for an additional 15 minutes. The reaction was concentrated and rinsed with diethyl ether. The resulting remaining precipitate was dried and further purified using HPLC to give the titled compound. LC-MS: 488.24 [M+H]. LC/MS RT=2.49 min.

Workup

additionwas added
concentrationThe reaction was concentrated
washrinsed with diethyl ether
customThe resulting remaining precipitate was dried
customfurther purified

Sources & evidence

ORD record: ord-40c27145af0f46938c98a5616f52a313
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351965B2

Reaction notes

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