N,N-dimethylazetidin-3-amine → 2-(3-(Dimethylamino)azetidin-1-yl)-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 924112Notes

Reaction equation

HRID 924112 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([F:14])[CH:13]=2)=[CH:6][C:5]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)=[O:16])=[CH:4][N:3]=1.[CH3:29][N:30]([CH3:35])[CH:31]1[CH2:34][NH:33][CH2:32]1>>[CH3:29][N:30]([CH3:35])[CH:31]1[CH2:34][N:33]([C:2]2[C:7]([C:8]3[CH:9]=[N:10][CH:11]=[C:12]([F:14])[CH:13]=3)=[CH:6][C:5]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:20][CH:19]=3)=[O:16])=[CH:4][N:3]=2)[CH2:32]1

Participants

3

Reactant 2

HCID 10351656N,N-dimethylazetidin-3-amineHCID 722015862-Chloro-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Product 1

HCID 1181951072-(3-(Dimethylamino)azetidin-1-yl)-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 236 using 2-chloro-5′-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3′-bipyridine]-5-carboxamide (Stage 236.1) and N,N-dimethylazetidin-3-amine. The crude product was purified by preparative HPLC (Condition 14). Fractions containing product were combined, treated with sat. aq. Na2CO3 and the MeCN was removed. The aq. phase was extracted with DCM and the combined organic layers were dried over Na2SO4, filtered and the filtrate was evaporated off under reduced pressure to afford the title product as white crystals. HPLC (Condition 10) tR=6.01 min, UPLC-MS (Condition 3) tR=0.82 min, m/z=476.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.99 (s, 6H) 2.95-3.04 (m, 1H) 3.53 (dd, J=9.19, 5.28 Hz, 2H) 3.69-3.77 (m, 2H) 7.36 (d, J=8.99 Hz, 2H) 7.87 (d, J=8.99 Hz, 3H) 8.08 (d, J=2.35 Hz, 1H) 8.54-8.57 (m, 1H) 8.63 (d, J=2.74 Hz, 1H) 8.79 (d, J=2.35 Hz, 1H) 10.23 (s, 1H).

Workup

  1. customThe title compound was prepared in an analogous fashion to
  2. customThe crude product was purified by preparative HPLC (Condition 14)
  3. additionFractions containing product
  4. additiontreated with sat. aq. Na2CO3
  5. customthe MeCN was removed
  6. extractionThe aq. phase was extracted with DCM
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. customthe filtrate was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-2d960e4311e74dd0a15141fe46761090
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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