HCID 90030495, compound → HCID 72944422, compound

HRID 531657Notes

Reaction equation

HRID 531657 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=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]([CH:38]=[CH:39][CH:40]=4)[O:24][CH:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:41])=[N:7]1>Cl.CO>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=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:40]=[CH:39][CH:38]=[C:23]([O:24][CH:25]5[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]5)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:41])=[N:7]1

Participants

4

Reactant 1

HCID 90030495HCID 90030495, compound

Product 1

HCID 72944422HCID 72944422, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 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)phenoxy)piperidine-1-carboxylate (80 mg, 0.134 mmol) was deprotected in HCl in methanol (5 ml). This afforded 33 mg (40.2% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.75-8.60 (bs, 1H), 8.37 (s, 1H), 7.66 (s, 1H), 7.48-7.44 (t, 1H), 7.42-7.37 (q, 1H), 7.33-7.29 (m, 2H), 7.11-7.04 (m, 3H), 6.93-6.91 (d, 1H), 5.41 (s, 2H), 4.85-4.82 (m, 1H), 3.48-3.41 (m, 2H), 3.28-3.23 (m, 2H), 2.25-2.28 (m, 8H), 2.12-2.06 (m, 2H). MS: m/z=496.3 (M+1), HPLC: 96.84% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d9aebb78c5f24a158116bcf222265dc1
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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