trans-3-Amino-4-methoxypyrrolidine dihydrochloride → HCID 118195351, compound

HRID 924147Notes

Reaction equation

HRID 924147 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.Cl.Cl.[CH3:31][O:32][C@@H:33]1[CH2:37][NH:36][CH2:35][C@H:34]1[NH2:38]>>[NH2:38][C@H:34]1[C@H:33]([O:32][CH3:31])[CH2:37][N:36]([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:19]=[CH:20][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=3)=[O:16])=[CH:4][N:3]=2)[CH2:35]1

Participants

3

Reactant 2

HCID 67925434trans-3-Amino-4-methoxypyrrolidine dihydrochlorideHCID 722015862-Chloro-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Product 1

HCID 118195351HCID 118195351, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 284 using 2-chloro-5′-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3′-bipyridine]-5-carboxamide (Stage 236.1) and trans-4-methoxypyrrolidin-3-amine dihydrochloride (Stage 284.1, 20 h at 80° C. then 24 h at 100° C.). HPLC (Condition 10) tR=5.97 min, UPLC-MS (Condition 3) tR=0.83 min, m/z=492.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.62 (br. s, 2H) 2.82-2.90 (m, 1H) 3.02-3.11 (m, 1H) 3.21 (s, 3H) 3.26-3.34 (m, 2H) 3.47-3.57 (m, 2H) 7.35 (d, J=8.99 Hz, 2H) 7.85 (m, J=9.00 Hz, 3H) 8.08 (d, J=2.35 Hz, 1H) 8.51 (s, 1H) 8.60 (d, J=2.74 Hz, 1H) 8.77 (d, J=1.95 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customStage 284.1, 20 h
  2. customat 80° C.
  3. custom24 h
  4. customat 100° C.

Sources & evidence

ORD record
ord-6d09fe297a5f4d3b8776a38202fa8753
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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