Hydrochloric Acid → 2-(2-(3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamido)acetic acid hydrochloride
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.[Cl:41]C(OCC)=O.Cl.[NH2:48][CH2:49][C:50]([O:52]C(C)(C)C)=[O:51].Cl>>[ClH:41].[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]([NH:48][CH2:49][C:50]([OH:52])=[O:51])=[O:30])=[CH:19][CH:18]=[CH:17][N:16]=2)[S:12][CH:13]=1Participants
Reactant 5
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 tert-butyl 2-aminoacetate hydrochloride (120 mg, 0.72 mmol) were reacted according to the method of Example 30 to provide 2-(2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamido)acetic acid hydrochloride (43.1 mg, 61.1% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 10.75 (bs, 1H), 8.54 (t, 1H), 7.95 (d, 1H), 7.55 (d, 1H), 7.35 (d, 1H), 7.22 (m, 1H), 7.17 (d, 1H), 7.06 (dd, 1H), 6.96 (dd, 1H), 6.78 (s, 1H), 5.29 (s, 2H), 4.57 (s, 2H), 3.90 (d, 1H), 3.62 (s, 2H), 2.30 (s, 3H). Mass spectrum (apci) m/z=443.0 (M+H-HCl).
Sources & evidence
- ORD record
- ord-fc9f7dcda57d42df85171a63c9df47d2
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933077B2
Reaction notes
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