HCID 118524040, compound → HCID 90031357, compound

HRID 531853Notes

Reaction equation

HRID 531853 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]6[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]6)=[CH:24][CH:23]=5)[CH:20]=4)[NH:15][CH:14]=3)[CH:10]=[N:9]2)=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:31]1[CH2:32][CH2:33][CH:28]([C:25]2[CH:24]=[CH:23][C:22]([C:19]3[CH:20]=[C:21]4[C:13]([C:11]5[CH:10]=[N:9][N:8]([CH2:7][C:4]6[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=6)[CH:12]=5)=[CH:14][NH:15][C:16]4=[N:17][CH:18]=3)=[CH:27][CH:26]=2)[CH2:29][CH2:30]1

Participants

3

Reactant 1

HCID 118524040HCID 118524040, compound

Product 1

HCID 90031357HCID 90031357, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(pyridin-4-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (120 mg, 0.224 mmol) was deprotected in TFA/DCM (5/5 ml) to afford 14 mg (14.3% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.78-8.76 (d, 2H), 8.53-8.51 (t, 2H), 8.35 (s, 1H), 8.07 (s, 1H), 7.75-7.70 (m, 5H), 7.43-7.41 (d, 2H), 5.78 (s, 2H), 3.55-3.51 (d, 2H), 3.21-3.13 (td, 2H), 3.03-2.95 (m, 1H), 2.03-1.90 (m, 2H). MS: m/z=435.6 (M+1), HPLC: 99.16% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9d2453bec025418893a29bc1155fba32
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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