Hydrochloric Acid → HCID 178484204, compound

HRID 1922467Notes

Reaction equation

HRID 1922467 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[NH:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][NH:14][CH3:15])[CH2:9][CH2:8][CH2:7]2.[ClH:24].C(OCC)C>CO>[ClH:24].[ClH:24].[F:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[NH:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][NH:14][CH3:15])[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178484203HCID 178484203, compound

Product 1

HCID 178484204HCID 178484204, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(8-fluoro-1-(2-(methylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (57 mg, 0.171 mmol) in Methanol (3 ml) was added hydrogen chloride, 1M in diethyl ether (0.514 ml, 0.514 mmol). The resulting solution was then concentrated to give the desired N-(8-fluoro-1-(2-(methylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide dihydrochloride (69 mg, 0.170 mmol, 99% yield). 1H NMR (DMSO-d6) δ 9.79 (s, 1H); 9.13 (brs, 2H); 8.84 (s, 1H); 8.16 (d, J=4.8 Hz); 7.37 (t, J=4.3 Hz, 1H); 7.14 (d, J=14 Hz, 1H); 6.94 (s, 1H); 3.47-3.40 (m, 2H); 3.24-3.18 (m, 2H); 3.18-3.10 (m, 2H); 2.76 (t, J=6 Hz, 2H); 2.58 (t, J=5.1 Hz, 3H); 1.85-1.78 (m, 2H). EI-MS (m/z, %): 332 (M+, 9); 288 (100). HRMS calculated for C17H21FN4S (M+), calculated: 332.1477, observed: 332.1471. HPLC purity: 95%.

Workup

  1. concentrationThe resulting solution was then concentrated

Sources & evidence

ORD record
ord-ebcc08c8178448398a5f6685f85063e7
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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