Hydrochloric Acid → HCID 90064824, compound

HRID 531535Notes

Reaction equation

HRID 531535 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:22]=[C:23]([N:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)[CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:40])=[N:7]1.Cl>CO>[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][CH:24]=[C:23]([N:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)[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 90031236HCID 90031236, compound

Product 1

HCID 90064824HCID 90064824, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (96 mg, 0.165 mmol) was deprotected in methanol (5 ml), HCl in dioaxane (5 ml). This afforded 20 mg (23.5% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.759-8.755 (d, 1H), 8.639-8.635 (d, 1H), 7.818 (s, 1H), 7.482-7.370 (m, 3H), 7.284-7.265 (d, 1H), 7.154-7.087 (m, 3H), 6.995-6.971 (m, 1H), 5.489 (s, 2H), 3.530-3.516 (m, 4H), 3.413-3.387 (m, 4H), 2.288 (s, 6H). MS: m/z=481.1 (M+1); HPLC: 85.59% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-371c4aabec344670b606bc347c4dbeb5
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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