HCID 90031422, compound → HCID 90031051, compound

HRID 531646Notes

Reaction equation

HRID 531646 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:40])=[N:7]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:40])=[N:7]1

Participants

3

Reactant 1

HCID 90031422HCID 90031422, compound

Product 1

HCID 90031051HCID 90031051, compoundYield 12.9%

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-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (113 mg, 0.194 mmol) was deprotected in TFA/DCM (5/5 ml). This afforded 12 mg (12.9% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.55 (s, 1H), 8.09-8.08 (d, 1H), 7.65-7.62 (m, 2H), 7.51 (s, 1H), 7.41-7.34 (m, 3H), 7.06-7.00 (m, 2H), 6.90-6.87 (s, 1H), 5.38 (s, 2H), 3.54-3.47 (m, 2H), 3.20-3.13 (m, 2H), 3.01-2.93 (m, 1H), 2.22 (s, 3H), 2.20 (s, 3H), 2.14-1.88 (m, 4H). MS: m/z=480.2 (M+1), HPLC: 98.73% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c5b459e8c83b483f822ea31342349091
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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