4-Bromo-3-fluorobenzoic acid → 4-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-cyclopropyl-3-fluoro-N-methylbenzamide
Reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].Cl.[CH3:13][NH:14][CH:15]1[CH2:17][CH2:16]1.Cl.Cl.C[Si](C)(C)CCOC[N:26]1[C:30]2[N:31]=[CH:32][N:33]=[C:34]([C:35]3[CH:36]=[N:37][N:38]([C:40]4([CH2:44][C:45]#[N:46])[CH2:43][NH:42][CH2:41]4)[CH:39]=3)[C:29]=2[CH:28]=[CH:27]1>>[C:45]([CH2:44][C:40]1([N:38]2[CH:39]=[C:35]([C:34]3[C:29]4[CH:28]=[CH:27][NH:26][C:30]=4[N:31]=[CH:32][N:33]=3)[CH:36]=[N:37]2)[CH2:43][N:42]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([N:14]([CH:15]3[CH2:17][CH2:16]3)[CH3:13])=[O:8])=[CH:4][C:3]=2[F:11])[CH2:41]1)#[N:46]Participants
4
Reactant 3
Product 1
Procedure
This compound was prepared by using procedures analogous to those described for the synthesis of Example 3, Step 1-3 starting from 4-bromo-3-fluorobenzoic acid, N-methylcyclopropanamine hydrochloride (J&W PharmLab: Cat. #20-0433S) and {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride. LCMS (M+H)+: m/z=471.2. 1H NMR (400 MHz, DMSO-D6): δ 12.83 (s, 1H), 9.17 (s, 1H), 8.91 (s, 1H), 8.60 (s, 1H), 7.85 (s, 1H), 7.33 (m, 3H), 6.71 (t, J=9.0 Hz, 1H), 4.66 (d, J=8.0 Hz, 2H), 4.41 (d, J=8.0 Hz, 2H), 3.79 (s, 2H), 2.97 (m, 1H), 2.93 (s, 3H), 0.59 (m, 2H), 0.42 (m, 2H).
Workup
- customThis compound was prepared
Sources & evidence
- ORD record
- ord-34d41959d6434829add804f5caf8f4d6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023840B2
Reaction notes
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