Hydrochloric Acid → HCID 118524079, compound

HRID 531538Notes

Reaction equation

HRID 531538 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]([N: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.[ClH:44]>O1CCOCC1>[ClH:44].[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]([N: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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118524091HCID 118524091, compound

Product 1

HCID 118524079HCID 118524079, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

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)piperazine-1-carboxylate (80 mg, 0.137 mmol) was deprotected in dioxane (1 ml), HCl in dioxane (3 ml). This afforded 5 mg (23.5% yield) of the titled compound. 1H NMR (DMSO-d6, 300 MHz): δ 9.14-9.0 (b, 1H), 8.54 (d, 1H), 7.92 (s, 1H), 7.63-7.60 (s 2H), 7.54-7.53 (s, 1H), 7.5 (m, 1H), 7.10-7.04 (m, 5H), 5.34 (s, 2H), 3.41 (m, 4H), 3.25 (m, 4H), 2.17-2.14 (d, 4H). MS: m/z=481.2 (M+1), HPLC: 90.3% in Method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c7a1cdd4ce144dae8327ae895b7983ff
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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