Hydrochloric Acid → HCID 118523972, compound

HRID 531545Notes

Reaction equation

HRID 531545 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[C:42]([F:44])[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:45]>CO>[ClH:45].[F:44][C:42]1[CH:41]=[C:4]([CH:3]=[C:2]([F:1])[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[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:40])=[N:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90030892HCID 90030892, compound

Product 1

HCID 118523972HCID 118523972, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (100 mg, 0.167 mmol) was deprotected in methanol (5 ml), HCl in 1,4-dioaxane (5 ml). This afforded 100 mg (63.3% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 8.56 (s, 1H), 7.858-7.853 (d, 1H), 7.54-7.51 (d, 2H), 7.03-7.01 (d, 2H), 6.69-6.67 (m, 2H), 5.29 (s, 2H), 3.65-3.59 (t, 4H), 3.21-3.19 (t, 4H), 2.26 (s, 3H), 2.15 (s, 3H), 1.49 (s, 9H). MS: m/z=599.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-686043e6f5a04007b2611f4609312a63
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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