(2R)-1,1,1-Trifluoropropan-2-amine--hydrogen chloride (1/1) → US9611269, Example 16

HRID 2363306Notes

Reaction equation

HRID 2363306 reaction equation
[C:1]([CH2:3][C:4]1([N:18]2[CH:22]=[C:21]([C:23]3[C:24]4[CH:31]=[CH:30][N:29](COCC[Si](C)(C)C)[C:25]=4[N:26]=[CH:27][N:28]=3)[CH:20]=[N:19]2)[CH2:7][N:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=2[F:17])[CH2:5]1)#[N:2].Cl.[F:41][C:42]([F:47])([F:46])[C@H:43]([NH2:45])[CH3:44]>>[C:1]([CH2:3][C:4]1([N:18]2[CH:22]=[C:21]([C:23]3[C:24]4[CH:31]=[CH:30][NH:29][C:25]=4[N:26]=[CH:27][N:28]=3)[CH:20]=[N:19]2)[CH2:7][N:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH:45][C@H:43]([CH3:44])[C:42]([F:47])([F:46])[F:41])=[O:14])=[CH:10][C:9]=2[F:17])[CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 44593757(2R)-1,1,1-Trifluoropropan-2-amine--hydrogen chloride (1/1)HCID 71143553HCID 71143553, compound

Product 1

HCID 71155851US9611269, Example 16

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 5, Step 3 starting from 4-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-3-fluorobenzoic acid and (2R)-1,1,1-trifluoropropan-2-amine hydrochloride. LCMS (M+H)+: m/z=513.2. 1H NMR (400 MHz, DMSO-d6): δ 12.66 (br, 1H), 9.11 (s, 1H), 8.86 (s, 1H), 8.64 (d, J=8.9 Hz, 1H), 8.58 (s, 1H), 7.80 (br, 1H), 7.71 (s, 1H), 7.69 (dd, J=4.0, 1.6 Hz, 1H), 7.26 (br, 1H), 6.78 (t, J=8.7 Hz, 1H), 4.89-4.78 (m, 1H), 4.71 (d, J=7.7 Hz, 2H), 4.45 (dd, J=9.4, 1.8 Hz, 2H), 3.78 (s, 2H), 1.35 (d, J=7.0 Hz, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-5e766a22467f4db1a7266653da0300de
Source dataset
uspto-grants-2014_04
Patent number
US08691807B2

Reaction notes

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