{3-[4-(7-{[2-(Trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride → 5-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide

HRID 571483Notes

Reaction equation

HRID 571483 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C@H:11]([CH:13]2[CH2:15][CH2:14]2)[CH3:12])=[O:9])=[N:6][CH:7]=1.Cl.Cl.C[Si](C)(C)CCOC[N:24]1[C:28]2[N:29]=[CH:30][N:31]=[C:32]([C:33]3[CH:34]=[N:35][N:36]([C:38]4([CH2:42][C:43]#[N:44])[CH2:41][NH:40][CH2:39]4)[CH:37]=3)[C:27]=2[CH:26]=[CH:25]1>>[C:43]([CH2:42][C:38]1([N:36]2[CH:37]=[C:33]([C:32]3[C:27]4[CH:26]=[CH:25][NH:24][C:28]=4[N:29]=[CH:30][N:31]=3)[CH:34]=[N:35]2)[CH2:41][N:40]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH:10][C@H:11]([CH:13]3[CH2:15][CH2:14]3)[CH3:12])=[O:9])=[N:6][CH:7]=2)[CH2:39]1)#[N:44]

Participants

3

Reactant 2

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 dihydrochlorideHCID 712079115-bromo-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide

Product 1

HCID 711553715-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 3, Step 2-3 starting from 5-bromo-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide (Example 2, Step 1) 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=468.2. 1H NMR (400 MHz, DMSO-d6): δ 12.60 (s, 1H), 9.14 (s, 1H), 8.90 (s, 1H), 8.60 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 7.97 (d, J=3.0 Hz, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.84 (m, 1H), 7.28 (m, 1H), 7.12 (dd, J=8.0, 3.0 Hz, 1H), 4.68 (d, J=8.0 Hz, 2H), 4.43 (d, J=8.0 Hz, 2H), 3.80 (s, 2H), 3.39 (m, 1H), 1.12 (t, J=7.0 Hz, 3H), 1.05 (m, 1H), 0.45 (m, 1H), 0.38 (m, 1H), 0.22 (m, 1H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-d51cfefd5fd04ec7909535cd842739fc
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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