Hydrochloric Acid → N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine trihydrochloride

HRID 604907Notes

Reaction equation

HRID 604907 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]4)=[C:20]([O:30][CH3:31])[CH:19]=3)[S:16][C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:32]>C(Cl)Cl.C(OCC)C>[ClH:32].[ClH:32].[ClH:32].[CH3:31][O:30][C:20]1[CH:19]=[C:18]([NH:17][C:15]2[S:16][C:10]3[CH2:9][NH:8][CH2:13][CH2:12][C:11]=3[N:14]=2)[CH:23]=[CH:22][C:21]=1[N:24]1[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25106279tert-Butyl 2-((3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate

Product 1

HCID 25106280N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine trihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1347 mg (3.05 mmol) 2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester was suspended in methylene chloride (30.5 ml) and 2M HCl in diethyl ether (15.3 ml) was added at room temperature. Initially a clear solution was obtained and then a solid precipitated. The reaction was stirred at room temperature over night. The reaction was diluted with diethyl ether, stirred for 15 minutes and the solid was filtered off, washed with diethyl ether and dried to yield 1370 mg (100%) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-amine trihydrochloride as a light yellow solid. MS ISP (m/e): 342.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.91 (s, 1H), 9.68 (br, 2H), 9.31 (s, 1H), 7.66 (s, 2H), 7.48 (d, 1H), 7.45 (d, 1H), 4.22 (br s, 2H), 3.84 (s, 3H), 3.38 (m, 2H), 2.88 (m, 2H), 2.35 (s, 3H).

Workup

  1. customInitially a clear solution was obtained
  2. customa solid precipitated
  3. additionThe reaction was diluted with diethyl ether
  4. stirringstirred for 15 minutes
  5. filtrationthe solid was filtered off
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-88af988630ea42568668410439728d4e
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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