Hydrochloric Acid → HCID 51354885, compound

HRID 1640180Notes

Reaction equation

HRID 1640180 reaction equation
Cl.[CH:2]1([C:5]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH2:20][CH:21]([C:25]([NH:27][C:28]5[CH:29]=[C:30]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=5)[CH2:31][NH:32]C(=O)OC(C)(C)C)=[O:26])[CH2:22]4)=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[O:6])[CH2:4][CH2:3]1>O1CCOCC1>[NH2:32][CH2:31][C:30]1[CH:29]=[C:28]([NH:27][C:25]([CH:21]2[CH2:20][CH2:19][C:18]3[C:23](=[CH:24][C:15]([O:14][C:12]4[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5]([CH:2]5[CH2:4][CH2:3]5)=[O:6])[CH:13]=4)=[CH:16][CH:17]=3)[CH2:22]2)=[O:26])[CH:42]=[C:41]([C:43]([F:44])([F:46])[F:45])[CH:40]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86613294HCID 86613294, compound

Product 1

HCID 51354885HCID 51354885, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4M HCl in dioxane (30 mL) was added to tert-butyl [3-({[7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbonyl}-amino)-5-(trifluoromethyl)benzyl]carbamate (3.80 g, 6.08 mmol). The suspension was allowed to stir for 2 h. The solvents were evaporated and the residue was purified by column chromatography to give N-[3-(aminomethyl)-5-(trifluoromethyl)phenyl]-7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxamide I-417 (2.60 g, 82%) as a white solid. The HCl salt was prepared by dissolving the solid in DCM and adding 2M HCl in Et2O. The solvents were evaporated. 1H NMR (400 MHz, d6-DMSO, HCl salt) δ: 11.62-11.77 (m, 1H), 10.77 (s, 1H), 8.43 (br s, 2H), 8.22 (d, 1H), 8.06 (s, 1H), 8.03 (s, 1H), 7.59 (s, 1H), 7.33 (s, 1H), 7.24 (d, 1H), 7.04-6.95 (m, 2H), 6.88-6.82 (m, 1H), 4.05-4.11 (m, 2H), 2.99-2.75 (m, 5H), 2.17-1.72 (m, 3H), and 0.91-0.80 (m, 4H). LCMS: (FA) ES+ 525.6, ES− 523.3.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-271c338a9d4f4aa5be68a00f03ee69f0
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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