HCID 57546213, compound → 2-(5-Chloro-1H-indazol-7-yl)-2-((4-(4-fluorophenyl)-1-methylpiperidin-4-yl)methoxy)acetonitrile

HRID 914039Notes

Reaction equation

HRID 914039 reaction equation
FC(F)(F)C(O)=O.ClC1C=C2C(=C(C(OCC3(C4C=CC(F)=CC=4)CCN(C)CC3)C(OC)=O)C=1)NN=C2.[Cl:39][C:40]1[CH:41]=[C:42]2[C:46](=[C:47]([CH:49]([C:72]#[N:73])[O:50][CH2:51][C:52]3([C:65]4[CH:70]=[CH:69][C:68]([F:71])=[CH:67][CH:66]=4)[CH2:57][CH2:56][N:55]([C:58](OC(C)(C)C)=O)[CH2:54][CH2:53]3)[CH:48]=1)[NH:45][N:44]=[CH:43]2>>[Cl:39][C:40]1[CH:41]=[C:42]2[C:46](=[C:47]([CH:49]([O:50][CH2:51][C:52]3([C:65]4[CH:70]=[CH:69][C:68]([F:71])=[CH:67][CH:66]=4)[CH2:53][CH2:54][N:55]([CH3:58])[CH2:56][CH2:57]3)[C:72]#[N:73])[CH:48]=1)[NH:45][N:44]=[CH:43]2

Participants

3

Reactant 2

HCID 57546213HCID 57546213, compoundHCID 67403905HCID 67403905, compound

Product 1

HCID 251612272-(5-Chloro-1H-indazol-7-yl)-2-((4-(4-fluorophenyl)-1-methylpiperidin-4-yl)methoxy)acetonitrile

Procedure

Prepared according to the procedure used to prepare methyl 2-(5-chloro-1H-indazol-7-yl)-2-((4-(4-fluorophenyl)-1-methylpiperidin-4-yl)methoxy)acetate trifluoroacetic acid salt using tert-butyl 4-(((5-chloro-1H-indazol-7-yl)(cyano)methoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate as the starting material. After preparative HPLC, the product was still impure. The product was re-purified by column chromatography (2M ammonia in methanol/dichloromethane) to give the title compound as the freebase. 1H-NMR (CDCl3, 500 MHz) δ 9.51 (bs, 1H), 7.97 (s, 1H), 7.73 (d, J=1.8 Hz, 1H), 7.34 (dd, J=8.9, 5.2 Hz, 2H), 7.31 (s, 1H), 7.14 (m, 2H), 5.43 (s, 1H), 3.84 (d, J=8.6 Hz, 1H), 3.68 (d, J=8.5 Hz, 1H), 2.56 (m, 2H), 2.22 (m, 8H), 1.99 (m, 3H), 1.67 (bs, 6H). Mass spec.: 413.22 (MH)+.

Workup

  1. customPrepared
  2. customThe product was re-purified by column chromatography (2M ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-4c0c7c87574742bdbda9478cc307e096
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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