Hydrochloric Acid → HCID 90313565, compound

HRID 1523856Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:21][S:22]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31]C(=O)OC(C)(C)C)[CH2:27][CH2:26]3)(=[O:24])=[O:23])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[ClH:39]>>[ClH:39].[NH2:31][CH:28]1[CH2:27][CH2:26][N:25]([S:22]([CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:11]2[CH:10]=[CH:9][C:8]([C:5]3[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[C:13]([F:14])[CH:12]=2)(=[O:23])=[O:24])[CH2:30][CH2:29]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 90314482HCID 90314482, compound

Product 1

HCID 90313565HCID 90313565, compoundYield 61%

Procedure

A mixture of tert-butyl 1-((4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-yl)methylsulfonyl)piperidin-4-ylcarbamate (190 mg, 0.35 mmol) in HCl (20 mL, 6 N in methanol) was stirred at rt for 24 hours. The solvent was removed under reduced pressure and the residue purified by HPLC to give the title compound (80 mg HCl salt, 61%). MS (ESI): mass calcd. for C22H24FN5O2S, 441.16; m/z found, 442.1 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 8.38 (s, 1H), 8.10 (br, 4H), 7.95 (m, 1H), 7.64-7.55 (m, 1H), 7.52-7.32 (m, 4H), 4.80 (br, 4H), 4.37 (s, 2H), 3.50 (d, J=13.0, 2H), 3.10 (s, 1H), 2.76 (t, J=12.6, 2H), 1.91 (d, J=11.0, 3H), 1.58-1.41 (m, 2H).

Workup

customThe solvent was removed under reduced pressure
customthe residue purified by HPLC

Sources & evidence

ORD record: ord-a6684467e635422684661c246922f415
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079866B2

Reaction notes

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