Hydrochloric Acid → HCID 25023854, compound

HRID 888011Notes

Reaction equation

HRID 888011 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:35])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][C:25]([CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:26][N:27]=2)=[CH:19][CH:18]=1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:35])[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[S:24][C:25]([CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:26][N:27]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68408078HCID 68408078, compound

Product 1

HCID 25023854HCID 25023854, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

N-(2-t-butoxycarbonylaminophenyl)-4-[5-(piperidin-1-ylmethyl)-1,3-thiazol-2-yl]benzamide (Method 51, 271 mg, 0.54 mmol) was suspended in 1,4 dioxane (4 ml) and a 4M solution of hydrogen chloride in 1,4-dioxane (4 ml) added. The reaction mixture was stirred at ambient temperature for 17 hours. The resultant precipitate was collected by filtration, washed with diethyl ether and air dried to yield the title compound as its hydrochloride salt. The crude solid was purified using an Oasis MCX column, eluting with methanol/dichloromethane (0-100%) then 2M ammonia in methanol/methanol (0-20%) to give the title compound as its free base (119 mg, 56%); NMR Spectrum: (DMSO-d6) 1.40 (m, 2H), 1.50 (m, 4H), 2.41 (m, 4H), 3.74 (s, 2H), 4.94 (s, 2H), 6.61 (t, 1H), 6.80 (d, 1H), 6.99 (t, 1H), 7.18 (d, 1H), 7.80 (s, 1H), 8.06 (d, 2H), 8.09 (d, 2H), 9.78 (s, 1H); Mass Spectrum: M+H+ 402.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with diethyl ether and air
  3. customdried

Sources & evidence

ORD record
ord-bd347311365e44ff97459067d9dc6541
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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