Tert-butyl 3-amino-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylate → 4-((4-(3-(Trifluoromethyl)phenyl)piperidin-3-yl)amino)benzo[d][1,2,3]triazine-8-carboxamide

HRID 59979Notes

Reaction equation

HRID 59979 reaction equation
O[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])=[O:13])[C:4]=2[N:5]=[N:6][N:7]=1.[NH2:15][CH:16]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1>>[F:31][C:28]([F:29])([F:30])[C:24]1[CH:23]=[C:22]([CH:21]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[NH:15][C:2]2[C:3]3[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])=[O:13])[C:4]=3[N:5]=[N:6][N:7]=2)[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 43811007Tert-butyl 3-amino-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylateHCID 1785136134-oxo-1H-1,2,3-benzotriazine-8-carboxamide

Product 1

HCID 760729944-((4-(3-(Trifluoromethyl)phenyl)piperidin-3-yl)amino)benzo[d][1,2,3]triazine-8-carboxamide

Procedure

Compound 21 was prepared following general synthesis scheme 9 wherein 4-hydroxybenzo[d][1,2,3]triazine-8-carboxylic acid amide was reacted with tert-butyl 3-amino-4-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate to give the title compound. LC-MS [417 (M+H)], 1H NMR (400 MHz, DMSO-d6) δ 9.24 (s, 1H), 8.98 (d, 1H), 8.84 (t, 1H), 8.54 (d, 1H), 8.50 (d, 1H), 8.30 (d, 1H), 8.04-7.89 (m, 2H), 7.67 (s, 1H), 7.59 (t, 1H), 7.45 (d, 2H), 5.42-5.26 (m, 1H), 3.64 (d, 1H), 3.49 (d, 1H), 3.35 (td, 1H), 3.23-2.90 (m, 2H), 2.52-2.00 (m, 2H).

Workup

  1. customCompound 21 was prepared

Sources & evidence

ORD record
ord-ad56ad7dfa584ebc9d82eeca90ce1478
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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