Hydrochloric Acid → Hydrochloric Acid

HRID 711976Notes

Reaction equation

HRID 711976 reaction equation
[OH:1][C@@H:2]([C:4]1[N:15]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)[C:7]2=[C:8]3[S:14][CH:13]=[CH:12][C:9]3=[N:10][CH:11]=[C:6]2[N:5]=1)[CH3:3].[ClH:25].O>C(#N)C>[ClH:25].[OH:1][C@@H:2]([C:4]1[N:15]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)[C:7]2=[C:8]3[S:14][CH:13]=[CH:12][C:9]3=[N:10][CH:11]=[C:6]2[N:5]=1)[CH3:3].[ClH:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 178462237HCID 178462237, compound

Product 2

HCID 313Hydrochloric AcidHCID 178462238HCID 178462238, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(trans-4-{2-[(1R)-1-Hydroxyethyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl}cyclohexyl)acetonitrile (0.154 g, 0.451 mmol) was dissolved in acetonitrile (10 mL). 1.0 M Hydrogen chloride in water (0.480 mL, 0.480 mmol) was added slowly with stirring, followed by addition of water (10 mL). The mixture was stirred at room temperature until becoming homogeneous. The resulting solution was lyophilized to give the desired product as HCl salt. (0.169 g, 99.5%). LCMS calculated for C18H21N4OS (M+H)+: m/z=341.1. Found: 341.1. 1H NMR (DMSO-d6, 500 MHz) δ 9.55 (1H, s), 8.47 (1H, d, J=5.5 Hz), 8.00 (1H, d, J=5.5 Hz), 5.32 (1H, m), 5.07 (1H, m), 2.62 (2H, d, J=6.0 Hz), 2.43 (2H, m), 2.12 (2H, m), 2.04 (3H, m), 1.68 (3H, d, J=6.0 Hz), 1.46 (2H, m) ppm.

Workup

  1. stirringThe mixture was stirred at room temperature

Sources & evidence

ORD record
ord-bf7774a7147d47d6949546f133ec703a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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