3-Methylazetidin-3-ol → HCID 89908132, compound

HRID 525703Notes

Reaction equation

HRID 525703 reaction equation
Cl[C:2]1[C:21]([C:22]2[N:26](C3CCCCO3)[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]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH3:33][C:34]1([OH:38])[CH2:37][NH:36][CH2:35]1>>[OH:38][C:34]1([CH3:33])[CH2:37][N:36]([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]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)=[O:7])=[CH:4][N:3]=2)[CH2:35]1

Participants

3

Reactant 2

HCID 115427823-Methylazetidin-3-olHCID 899080896-chloro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89908132HCID 89908132, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 33 using 6-chloro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 32.1) and 3-methylazetidin-3-ol to afford an off-white powder. HPLC (Condition 4) tR=4.52 min, UPLC-MS (Condition 3) tR=0.88 min, m/z=434.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.30 (s, 3H) 3.61 (s, 4H) 5.40 (s, 1H) 6.41 (s, 1H) 7.32 (d, J=8.60 Hz, 2H) 7.74-7.89 (m, 3H) 8.04 (d, J=2.35 Hz, 1H) 8.70 (s, 1H) 10.20 (s, 1H) 12.90-13.15 (m, 1H).

Workup

  1. customto afford an off-white powder

Sources & evidence

ORD record
ord-3005613c83bb4dcbbecb3278e95ff1a1
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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