Hydrochloric Acid → N-{4-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]pyridin-2-yl}cyclopropanecarboxamide

HRID 1640194Notes

Reaction equation

HRID 1640194 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:23]=[C:22]4[C:17]([CH2:18][CH2:19][CH:20]([NH:24]C(=O)OC(C)(C)C)[CH2:21]4)=[CH:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.Cl>O1CCOCC1>[NH2:24][CH:20]1[CH2:21][C:22]2[CH:23]=[C:14]([O:13][C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])[CH:12]=3)[CH:15]=[CH:16][C:17]=2[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58902285Tert-butyl [7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Product 1

HCID 58902432N-{4-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]pyridin-2-yl}cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl [7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (4.0 g, 0.0071 mol) was added HCl in dioxane (4M, 15 ml). After 2 h at rt, the solvent was removed. N-{4-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]pyridin-2-yl}cyclopropanecarboxamide was obtained as off white solid and was used without further purification (2.8 g). 1H NMR (d6-DMSO, 400MHz, HCl salt) δ: 11.50 (s, 1H); 8.25 (s, 2H); 7.40 (s, 1H); 7.24 (d, 1H); 7.04 (d, 1H); 6.80 (dd, 1H); 6.82 (dd, 1H); 4.35 (s, 1H); 3.45 (s, 1H); 2.90 (dd, 1H); 2.85 (m, 3H); 2.14 (m, 1H); 1.95 (m, 1H); 1.77 (m, 1H); and 0.83 (m, 4H). LCMS ES+ 324.4, ES− 322.5

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-31e9dd3346dc43e0b4bcd0ba7f3f8e17
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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