Hydrochloric Acid → HCID 178480162, compound

HRID 1922479Notes

Reaction equation

HRID 1922479 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[NH:22])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[CH2:9][CH2:8][CH2:7]2.C(OCC)C.[ClH:33]>CO>[ClH:33].[ClH:33].[F:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[NH:22])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178480161HCID 178480161, compound

Product 1

HCID 178480162HCID 178480162, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (485 mg, 1.255 mmol) was dissolve in a mixture of methanol (2.5 ml) and hydrogen chloride, 1.0 M in diethyl ether (2.510 ml, 2.510 mmol). The solution was then concentrated, giving the desired N-(8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide dihydrochloride 55 (575 mg, 1.251 mmol, 100% yield). 1H NMR (DMSO-d6) δ 11.44 (brs, 1H), 11.07 (m, 1H), 9.79 (brs, 1H), 8.82 (brs, 1H), 8.16 m, 2H), 7.36 (t, J=4.4 Hz, 1H), 7.10 (d, J=13 Hz, 1H), 6.91 (brs, 1H), 4.19 (brs, 2H), 3.54-3.47 (m, 1H), 3.25-3.16 (m, 5H), 3.02-2.96 (m, 1H), 2.77-2.73 (m, 5H), 2.29-2.22 (m, 2H), 1.97-1.91 (m, 3H), 1.85-1.81 (m, 2H), 1.72-1.64 (m, 1H). MS-EI+ (m/z, %) 386 (100, M+), 288 (55), 275 (82), 111 (68), 84 (64). EI+-HRMS calculated for C21H27FN4S+ (M+) calculated: 386.1938, observed: 386.1940.

Workup

  1. concentrationThe solution was then concentrated

Sources & evidence

ORD record
ord-de06fcd62f8345328dde5f889255e114
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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