Isopropylamine → 5-Chloro-4-{3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-2-fluoro-N-isopropylbenzamide
Reaction equation
Cl[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:12])[CH:3]=1.[CH3:13][CH:14]([NH2:16])[CH3:15].Cl.Cl.C[Si](C)(C)CCOC[N:25]1[C:29]2[N:30]=[CH:31][N:32]=[C:33]([C:34]3[CH:35]=[N:36][N:37]([C:39]4([CH2:43][C:44]#[N:45])[CH2:42][NH:41][CH2:40]4)[CH:38]=3)[C:28]=2[CH:27]=[CH:26]1>>[Cl:11][C:10]1[C:2]([N:41]2[CH2:42][C:39]([CH2:43][C:44]#[N:45])([N:37]3[CH:38]=[C:34]([C:33]4[C:28]5[CH:27]=[CH:26][NH:25][C:29]=5[N:30]=[CH:31][N:32]=4)[CH:35]=[N:36]3)[CH2:40]2)=[CH:3][C:4]([F:12])=[C:5]([CH:9]=1)[C:6]([NH:16][CH:14]([CH3:15])[CH3:13])=[O:8]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 4,5-dichloro-2-fluorobenzoic acid (Ark Pharm, Inc., Cat. #: AK-29091), 2-propanamine 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=493.2/495.2. 1H NMR (400 MHz, DMSO-d6): δ 12.65 (s, 1H), 9.09 (s, 1H), 8.85 (s, 1H), 8.56 (s, 1H), 7.86 (dd, J=8.0, 2.5 Hz, 1H), 7.78 (m, 1H), 7.52 (d, J=7.0 Hz, 1H), 7.23 (m, 1H), 6.64 (d, J=12.0 Hz, 1H), 4.77 (d, J=9.0 Hz, 2H), 4.51 (d, J=9.0 Hz, 2H), 3.75 (s, 2H), 4.00 (m, 1H), 1.12 (d, J=6.5 Hz, 6H).
Workup
- customThis compound was prepared
Sources & evidence
- ORD record
- ord-21537c31b401400c93634ea1fcd01dab
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023840B2
Reaction notes
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