Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86271014, compound

HRID 517684Notes

Reaction equation

HRID 517684 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=2)[C@@H:9]1[CH3:25])=[O:7])(C)(C)C.CC1C=C(C)N=C(N[C@@H]2CCCN(C([C:43]3[CH:48]=[CH:47][C:46](F)=[CH:45][C:44]=3[N:50]3[N:54]=[CH:53][CH:52]=[N:51]3)=O)[C@H]2C)N=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[N:51]1[N:50]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][N:16]=3)[C@@H:9]2[CH3:25])=[O:7])[N:54]=[CH:53][CH:52]=1

Participants

5

Reactant 4

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90442575HCID 90442575, compoundHCID 131733352HCID 131733352, compound

Product 1

HCID 86271014HCID 86271014, compound

Procedure

(±)-trans-tert-butyl-2-methyl-3-((5-(trifluoromethyl)pyridin-2-yl)amino)piperidine-1-carboxylate. Prepared analogous to Example 1 substituting (±)-trans-(3-((4,6-dimethylpyrimidin-2-yl)amino)-2-methylpiperidin-1-yl)(4-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone with the title compound from Step B, intermediate A-1 with intermediate A-4 and HATU with HBTU. MS (ESI) mass calcd. for C21H21F3N6O, 430.2; m/z found 431.2 [M+H]+. MP=154.7° C. (Mixture of 4 isomers, undefined ratio). 1H NMR (300 MHz, DMSO) δ 8.36 (d, J=21.8 Hz, 0.44H), 8.24 (d, J=12.9 Hz, 0.36H), 8.08 (d, J=1.3 Hz, 1.62H), 7.97 (s, 0.47H), 7.91 (d, J=8.2 Hz, 0.41H), 7.83-7.32 (m, 4.20H), 7.32-7.21 (m, 0.48H), 7.06-6.96 (m, 0.47H), 6.82 (d, J=8.9 Hz, 0.76H), 6.71 (dd, J=13.9, 7.0 Hz, 0.59H), 6.60 (s, 0.10H), 6.15 (d, J=8.8 Hz, 0.10H), 4.93 (d, J=6.0 Hz, 0.12H), 4.68 (q, J=6.8 Hz, 0.39H), 4.41 (t, J=13.4 Hz, 0.65H), 4.17-3.83 (m, 0.78H), 3.81-3.61 (m, 0.73H), 3.20 (d, J=14.4 Hz, 0.35H), 2.94 (t, J=11.7 Hz, 0.52H), 2.85-2.66 (m, 0.46H), 2.19-1.49 (m, 3.53H), 1.49-1.22 (m, 2.07H), 0.74 (d, J=6.9 Hz, 1.40H).

Sources & evidence

ORD record
ord-f6d80717ca674e2294037e209b411169
Source dataset
uspto-grants-2015_08
Patent number
US09115117B2

Reaction notes

Loading…