Hydrochloric Acid → N-(2-(dimethylamino)ethyl)-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamide dihydrochloride
Reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[N:10]=[C:11]([NH:14][C:15]2[C:20]([O:21][CH2:22][C:23]3[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=3)[O:26][CH2:27][C:28]([OH:30])=O)=[CH:19][CH:18]=[CH:17][N:16]=2)[S:12][CH:13]=1.C(N(CC)CC)C.[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44][NH2:45].[ClH:47]>>[ClH:47].[ClH:47].[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44][NH:45][C:28](=[O:30])[CH2:27][O:26][C:25]1[CH:31]=[CH:32][CH:33]=[C:23]([CH2:22][O:21][C:20]2[C:15]([NH:14][C:11]3[S:12][CH:13]=[C:9]([CH3:8])[N:10]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:24]=1Participants
Reactant 4
Product 1
Procedure
2-(3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetic acid trifluoroacetate (prepared according to Example 26; 70 mg, 0.14 mmol), triethylamine (0.10 mL, 0.72 mmol) ethyl chloroformate (0.035 mL, 0.36 mmol) and N1,N1-dimethylethane-1,2-diamine (0.079 mL, 0.72 mmol) were reacted according to the method of Example 30 to provide N-(2-(dimethylamino)ethyl)-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamide dihydrochloride (43.8 mg, 56.1% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 11.54 (bs, 1H), 10.76 (bs, 1H), 8.54 (t, 1H), 8.00 (d, 1H), 7.66 (d, 1H), 7.32 (m, 2H), 7.18 (m, 2H), 6.97 (dd, 1H), 6.93 (s, 1H), 5.34 (s, 2H), 4.60 (s, 2H), 3.53 (q, 2H), 3.19 (q, 2H), 2.76 (s, 6H), 2.35 (s, 3H). Mass spectrum (apci) m/z 442.1 (M+H-2HCl).
Sources & evidence
- ORD record
- ord-35d260782bc74c1dae85766464a8cabd
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933077B2
Reaction notes
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