Trifluoroacetic acid → US9611269, Example 10

HRID 571482Notes

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:54]=[CH:53][C:43]([C:44]([NH:46][C@@H:47]([CH3:52])[C:48]([F:51])([F:50])[F:49])=[O:45])=[CH:42][C:41]=1[F:55]>>[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:54]=[CH:53][C:43]([C:44]([NH:46][C@@H:47]([CH3:52])[C:48]([F:51])([F:50])[F:49])=[O:45])=[CH:42][C:41]=2[F:55])[CH2:33]1)#[N:36]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 67391464{3-[4-(7-{[2-(Trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride

HCID 711435284-bromo-3-fluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]benzamide

Product 1

HCID 71155796US9611269, Example 10

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-3-fluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]benzamide (from Step 1, above). LCMS (M+H)+: m/z=513.2. 1H NMR (300 MHz, DMSO-d6): δ 12.64 (s, 1H), 9.08 (s, 1H), 8.83 (s, 1H), 8.61 (d, J=8.5 Hz, 1H), 8.57 (s, 1H), 7.79 (m, 1H), 7.70 (s, 1H), 7.66 (m, 1H), 7.23 (d, J=2.3 Hz, 1H), 6.76 (t, J=8.5 Hz, 1H), 4.80 (m, 1H), 4.68 (d, J=8.0 Hz, 2H), 4.53 (d, J=8.0 Hz, 2H), 3.76 (s, 2H), 1.32 (d, J=7.0 Hz, 3H).

Sources & evidence

ORD record: ord-f8b1b5a7423e45bf90886132e4ea5e89
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023840B2

Reaction notes

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