Hydrochloric Acid → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride

HRID 1184906Notes

Reaction equation

HRID 1184906 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:36])=[C:16]([NH:18][C:19]([C:21]2[S:35][C:24]3=[N:25][C:26]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[CH:27][N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].[ClH:40]>O1CCOCC1>[ClH:40].[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:36])=[C:16]([NH:18][C:19]([C:21]2[S:35][C:24]3=[N:25][C:26]([NH:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34])=[CH:27][N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67125549N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide

Product 1

HCID 67125561N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 96c (8 mg, 0.015 mmol) was dissolved in dioxane (0.5 mL), 4N HCl (1 eq) was added and stirred for 1 h. Evaporated to dryness to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride 96d (9 mg, 100%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.24 (s, 3H), 2.84 (d, J=4.7 Hz, 6H), 3.33 (dt, J=5.9 Hz and 5.4 Hz, 2H), 3.75 (dt, J=5.9 Hz and 5.4 Hz, 2H), 7.28 (d, J=8.6 Hz, 1H), 7.60 (m, 2H), 7.75 (d, J=7.8 Hz, 1H), 7.86 (d, J=1.6 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.18 (s, 1H), 8.21 (t, J=5.4 Hz, 1H), 8.32 (s, 1H), 10.09 (br s, 1H), 10.19 (s, 1H), 10.38 (s, 1H).

Workup

  1. customEvaporated to dryness

Sources & evidence

ORD record
ord-4725d78070f147dc8c1393725ee8f18d
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

Loading…