Hydrogen chloride-ethyl acetate → HCID 18537340, compound

HRID 2186622Notes

Reaction equation

HRID 2186622 reaction equation
C(OC([NH:8][C:9](=[NH:37])[C:10]1[S:11][C:12]([S:35][CH3:36])=[C:13]([C:15]2[N:16]=[C:17]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH:30]([CH3:34])[CH2:29]4)[CH:22]=3)[S:18][CH:19]=2)[CH:14]=1)=O)(C)(C)C.[ClH:38].C(OCC)(=O)C>>[ClH:38].[CH3:34][CH:30]1[CH2:31][CH2:32][CH2:33][N:28]([CH2:27][C:23]2[CH:22]=[C:21]([NH:20][C:17]3[S:18][CH:19]=[C:15]([C:13]4[CH:14]=[C:10]([C:9]([NH2:37])=[NH:8])[S:11][C:12]=4[S:35][CH3:36])[N:16]=3)[CH:26]=[CH:25][CH:24]=2)[CH2:29]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 140421368HCID 140421368, compound

Product 1

HCID 18537340HCID 18537340, compoundYield 100%

Procedure

4-[2-({3-[(3-Methylpiperidyl)methyl]phenyl}amino)(1,3-thiazol-4-yl)]-5-methlylthiothiophene-2-carboxamidine hydrochloride: (tert-Butoxy)-N-(imino{4-[2-({3-[(3-methylpiperidyl)methyl]phenyl}amino)(1,3-thiazol-4-yl)]-5-methylthio(2-thienyl)}methyl)carboxamide (8.2 mg, 0.014 mmol) was stirred 2 mL of a 10% 3N HCl-ethyl acetate solution at 0° C. for 30 min., at which time the solvent was removed in vacuo to give 8 mg (100% yield) of the 4-[2-({3-[(3-methylpiperidyl)methyl]phenyl}amino)(1,3-thiazol-4-yl)]-5-methylthiothiophene-2-carboxamidine hydrochloride. 1H NMR (DMSO-d6, 300 MHz) δ 0.83 (d, 3H, J=5.6 Hz), 1.54-2.48 (m, 5H), 2.52-2.63 (m, 4H), 2.66 (s, 3H), 4.23 (d, 2H, J=4.8 Hz), 7.15-7.23 (m, 2H), 7.41 (t, 1H, J=7.8 Hz), 7.86-7.92 (m, 2H), 8.63 (s, 1H), 9.01 (bs, 2H), 9.42 (bs, 2H), 10.63 (s, 1H); (Mass Spectrum (ESI) m/z calcd. for C22H27N5S3, 457.7 (M+H), found 458.2.

Workup

  1. customat which time the solvent was removed in vacuo

Sources & evidence

ORD record
ord-8a0947f7aa104546bb683937a328675a
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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