Trifluoroacetic acid → N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine

HRID 63361

Reaction equation

HRID 63361 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([CH2:23][O:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([NH:35]C(=O)OC(C)(C)C)=[CH:27][CH:26]=3)[CH:20]=[CH:19][N:18]=2)[CH:13]=[N:12][CH:11]=1)[CH3:9]>C(Cl)Cl>[NH2:35][C:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]([O:24][CH2:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:14]3[CH:13]=[N:12][CH:11]=[C:10]([CH2:8][CH3:9])[N:15]=3)[CH:22]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118317293Tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate2×

Product 1

HCID 118305959N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amineYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.485 mL, 19.09 mmol) was added to a solution of tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate (Intermediate D (protected)) (360 mg, 0.763 mmol) in DCM (15 mL), and the reaction mixture stirred at room temperature for 4 h, then concentrated in vacuo. The residue was combined with sat. sodium hydrogencarbonate solution and stirred at room temperature for 16 h. The solid was filtered, washing with acetonitrile, and dried under vacuum to give the subtitle compound N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine as a beige solid (200 mg, 69%); Rt 2.14 min (Method 2); m/z 372 (M+H)+ (ES+); 1H NMR δ: 1.20 (3H, t), 2.64 (2H, q), 5.18-5.24 (4H, overlapping m), 6.59 (1H, d), 6.82 (1H, d), 7.03 (1H, d), 7.41-7.51 (2H, overlapping m), 7.98-8.01 (2H, m), 8.04 (1H, m), 8.22-8.29 (2H, overlapping m), 8.91 (1H, s), 10.04 (1H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringstirred at room temperature for 16 h
  3. filtrationThe solid was filtered
  4. washwashing with acetonitrile
  5. customdried under vacuum

Sources & evidence

ORD record
ord-291dceeaa8ca472d938abcb908bbdb3a
Source dataset
uspto-grants-2016_09
Patent number
US09447076B2

Linked notes

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