(Azetidin-3-yl)methanol hydrochloride → N-(4-(Chlorodifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)azetidin-1-yl)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525734Notes

Reaction equation

HRID 525734 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.[NH:28]1[CH2:31][CH:30]([CH2:32][OH:33])[CH2:29]1>>[Cl:19][C:16]([F:18])([F:17])[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:20]=[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)[C:2]([N:28]3[CH2:31][CH:30]([CH2:32][OH:33])[CH2:29]3)=[N:3][CH:4]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 24801400(Azetidin-3-yl)methanol hydrochlorideHCID 722015896-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 89908249N-(4-(Chlorodifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)azetidin-1-yl)-5-(1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 63 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide (Stage 48.1) and 3-azetidinemethanol hydrochloride to afford a yellow foam. HPLC (Condition 7) tR=5.51 min, UPLC-MS (Condition 3) tR=0.89 min, m/z=450.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.55-2.68 (m, 1H) 3.43-3.49 (m, 2H) 3.49-3.56 (m, 2H) 3.73-3.82 (m, 2H) 4.66-4.73 (m, 1H) 6.42 (br.s, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.79-7.91 (m, 3H) 8.04 (d, J=2.35 Hz, 1H) 8.75 (br.s, 1H) 10.21 (s, 1H) 13.02 (s, 1H).

Workup

  1. customto afford a yellow foam

Sources & evidence

ORD record
ord-0cc068f83d4b48d5ad7152c5ed8a7166
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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