trans-3-Amino-4-methoxypyrrolidine dihydrochloride → 6-(trans-3-Amino-4-methoxypyrrolidin-1-yl)-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525758Notes

Reaction equation

HRID 525758 reaction equation
Cl[C:2]1[C:21]([C:22]2[NH:26][N:25]=[CH:24][CH:23]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.Cl.Cl.[CH3:29][O:30][C@@H:31]1[CH2:35][NH:34][CH2:33][C@H:32]1[NH2:36]>>[NH2:36][C@H:32]1[C@H:31]([O:30][CH3:29])[CH2:35][N:34]([C:2]2[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)=[CH:20][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=3)=[O:7])=[CH:4][N:3]=2)[CH2:33]1

Participants

3

Reactant 2

HCID 67925434trans-3-Amino-4-methoxypyrrolidine dihydrochlorideHCID 722015896-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 899083266-(trans-3-Amino-4-methoxypyrrolidin-1-yl)-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 48 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide (Stage 48.1) and trans-4-methoxypyrrolidin-3-amine dihydrochloride (Stage 78.1) to afford a beige solid. HPLC (Condition 7) tR=5.797 min, UPLC-MS (Condition 3) tR=0.81 min, m/z=479.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.86-2.98 (m, 1H) 3.06-3.19 (m, 1H) 3.21 (s, 3H) 3.25-3.43 (m, 2H) 3.43-3.59 (m, 2H) 6.32-6.46 (m, 1H) 7.32 (d, J=8.60 Hz, 2H) 7.50-7.92 (m, J=8.99 Hz, 3H) 8.03 (s, 1H) 8.62-8.86 (m, 1H) 10.18 (s, 1H) 12.72-13.25 (m, 1H).

Workup

  1. customto afford a beige solid

Sources & evidence

ORD record
ord-ddda9486ede244b4ba060f9882e082cc
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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