2-Propanamine, 1,1,1-trifluoro-, hydrochloride (1:1), (2S)- → US9611269, Example 35

HRID 571534Notes

Reaction equation

HRID 571534 reaction equation
[C:1]([CH2:3][C:4]1([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[N:28](COCC[Si](C)(C)C)[CH:29]=[CH:30][C:23]=34)[CH:19]=[N:18]2)[CH2:7][N:6]([C:8]2[N:9]=[CH:10][C:11]([C:14](O)=[O:15])=[N:12][CH:13]=2)[CH2:5]1)#[N:2].Cl.[F:40][C:41]([F:46])([F:45])[C@@H:42]([NH2:44])[CH3:43]>>[C:1]([CH2:3][C:4]1([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[NH:28][CH:29]=[CH:30][C:23]=34)[CH:19]=[N:18]2)[CH2:7][N:6]([C:8]2[N:9]=[CH:10][C:11]([C:14]([NH:44][C@@H:42]([CH3:43])[C:41]([F:46])([F:45])[F:40])=[O:15])=[N:12][CH:13]=2)[CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 130939192-Propanamine, 1,1,1-trifluoro-, hydrochloride (1:1), (2S)-HCID 711435965-{3-(cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}pyrazine-2-carboxylic acid

Product 1

HCID 71155790US9611269, Example 35

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 34, Step 3 starting from 5-{3-(cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}pyrazine-2-carboxylic acid and (2S)-1,1,1-trifluoropropan-2-amine hydrochloride. LCMS (M+H)+: m/z=496.1. 1H NMR (400 MHz, DMSO-d6) δ 12.23 (br, 1H), 8.99 (s, 1H), 8.83 (d, J=9.3 Hz, 1H), 8.69 (d, J=1.4 Hz, 1H), 8.47 (s, 1H), 8.32 (d, J=5.6 Hz, 1H), 8.02 (d, J=1.4 Hz, 1H), 7.67 (dd, J=3.3, 2.6 Hz, 1H), 7.55 (d, J=5.5 Hz, 1H), 7.09 (dd, J=3.4, 1.7 Hz), 4.83 (d, J=10.0 Hz, 2H), 4.80 (m, 1H), 4.57 (d, J=9.6 Hz, 2H), 3.78 (s, 2H), 1.36 (d, J=7.2 Hz, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-28fd6575cb944c69896c690106101127
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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