Trifluoroacetic acid → 4-{3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1R)-1-cyclopropylethyl]-3-fluorobenzamide
Reaction equation
C(O)(C(F)(F)F)=O.Cl.Cl.C[Si](C)(C)CCOC[N:16]1[C:20]2[N:21]=[CH:22][N:23]=[C:24]([C:25]3[CH:26]=[N:27][N:28]([C:30]4([CH2:34][C:35]#[N:36])[CH2:33][NH:32][CH2:31]4)[CH:29]=3)[C:19]=2[CH:18]=[CH:17]1.Br[C:40]1[CH:53]=[CH:52][C:43]([C:44]([NH:46][C@@H:47]([CH:49]2[CH2:51][CH2:50]2)[CH3:48])=[O:45])=[CH:42][C:41]=1[F:54]>>[C:35]([CH2:34][C:30]1([N:28]2[CH:29]=[C:25]([C:24]3[C:19]4[CH:18]=[CH:17][NH:16][C:20]=4[N:21]=[CH:22][N:23]=3)[CH:26]=[N:27]2)[CH2:31][N:32]([C:40]2[CH:53]=[CH:52][C:43]([C:44]([NH:46][C@@H:47]([CH:49]3[CH2:51][CH2:50]3)[CH3:48])=[O:45])=[CH:42][C:41]=2[F:54])[CH2:33]1)#[N:36]Participants
Reactant 3
Product 1
Procedure
This compound was prepared as TFA salt by using procedures analogous to those described for the synthesis of Example 3, Step 2-3 starting from {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride and 4-bromo-N-[(1R)-1-cyclopropylethyl]-3-fluorobenzamide (from Step 1, above). LCMS (M+H)+: m/z=485.2. 1H NMR (400 MHz, DMSO-d6): δ 12.67 (s, 1H), 9.01 (s, 1H), 8.88 (s, 1H), 8.46 (s, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.71 (t, J=2.5 Hz, 1H), 7.52 (s, 1H), 7.48 (s, 1H), 7.17 (d, J=2.5 Hz, 1H), 6.61 (t, J=8.4 Hz, 1H), 4.53 (d, J=8.0 Hz, 2H), 4.28 (d, J=8.0 Hz, 2H), 3.63 (s, 2H), 3.28 (m, 1H), 1.04 (d, J=6.5 Hz, 6H), 0.82 (m, 1H), 0.30 (m, 1H), 0.20 (m, 1H), 0.06 (m, 1H), 0.01 (m, 1H).
Sources & evidence
- ORD record
- ord-25d5fbd742fa4f61ba4fcdabe739bade
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691807B2
Reaction notes
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