4-(Trifluoromethoxy)benzylamine → HCID 90411136, compound

HRID 1527761Notes

Reaction equation

FC(F)(F)OC1C=CC(CN)=CC=1.FC1C=C(C=CC=1[N+]([O-])=O)OCC1C=CN(C)N=1.[CH3:32][N:33]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:45]=[C:44]([NH:46][CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][C:55]([F:58])([F:57])[F:56])=[CH:50][CH:49]=3)[C:43]([NH2:59])=[CH:42][CH:41]=2)=[N:34]1.[CH3:60][C:61]1([CH3:69])[C@@H:66]2[C@H:62]1[C:63](=[O:68])[O:64][C:65]2=O>>[CH3:60][C:61]1([CH3:69])[C@H:66]([C:65]2[N:46]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][C:55]([F:56])([F:57])[F:58])=[CH:50][CH:49]=3)[C:44]3[CH:45]=[C:40]([O:39][CH2:38][C:35]4[CH:36]=[CH:37][N:33]([CH3:32])[N:34]=4)[CH:41]=[CH:42][C:43]=3[N:59]=2)[C@@H:62]1[C:63]([OH:68])=[O:64]

Participants

Reactant 4

HCID 5718464-(Trifluoromethoxy)benzylamine

HCID 12851675HCID 12851675, compound

HCID 828819703-((3-Fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole

HCID 90411017HCID 90411017, compound

Product 1

HCID 90411136HCID 90411136, compound

Procedure

The title compound was prepared using analogous conditions described for Example 1 using (4-(trifluoromethoxy)phenyl)methanamine and 3-((3-fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole in Step A then for Intermediate I using 5-((1-methyl-1H-pyrazol-3-yl)methoxy)-N1-(4-(trifluoromethoxy)benzyl)benzene-1,2-diamine and cis-6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione followed by the hydrolysis according to Example Example 111. MS (ESI): mass calcd. for C26H25F3N4O4, 514.18; m/z found, 515.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.60 (d, J=8.9, 1H), 7.33 (d, J=2.2, 1H), 7.21 (d, J=8.1, 2H), 7.09 (d, J=8.8, 2H), 7.06 (dd, J=8.9, 2.3, 1H), 6.94 (d, J=2.2, 1H), 6.31 (d, J=2.2, 1H), 5.39 (d, J=16.9, 1H), 5.31 (d, J=16.9, 1H), 5.09 (s, 2H), 3.86 (s, 3H), 2.31 (d, J=8.2, 1H), 2.04 (d, J=8.3, 1H), 1.20 (s, 3H), 0.97 (s, 3H).

Sources & evidence

ORD record: ord-cd05aaa5f2e24c838f0c012e2f76a459
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09089569B2

Reaction notes

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