Trifluoroacetic acid → HCID 68073644, compound

HRID 530883Notes

Reaction equation

HRID 530883 reaction equation
[F:1][C:2]1[CH:54]=[CH:53][CH:52]=[CH:51][C:3]=1[CH2:4][C:5]1([CH2:49][OH:50])[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:54]=[CH:53][CH:52]=[CH:51][C:3]=1[CH2:4][C:5]1([CH2:49][OH:50])[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

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68073646HCID 68073646, compound

Product 1

HCID 68073644HCID 68073644, compound

Procedure

In a flask, N-(3-(2-fluorobenzyl)-3-(hydroxymethyl)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: 474.22 [M+H]. LC/MS RT=2.18 min.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated
  3. washrinsed with diethyl ether
  4. customThe resulting remaining precipitate was dried
  5. customfurther purified

Sources & evidence

ORD record
ord-5ee6bc57d94842c58fe83960436bc253
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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