Hydrochloric Acid → N-(2-(1H-imidazol-5-yl)ethyl)-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamide dihydrochloride

HRID 1426113Notes

Reaction equation

HRID 1426113 reaction equation
[ClH:1].Cl.CN1[CH2:9][CH2:8][N:7]([C:10](=[O:34])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][C:21]3[C:22]([NH:27][C:28]4[S:29][CH:30]=[C:31]([CH3:33])[N:32]=4)=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:14]=2)CC1.C(N(CC)CC)C.[NH:42]1[C:46](CCN)=[CH:45][N:44]=[CH:43]1.Cl>>[ClH:1].[ClH:1].[NH:42]1[C:46]([CH2:9][CH2:8][NH:7][C:10](=[O:34])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][C:21]3[C:22]([NH:27][C:28]4[S:29][CH:30]=[C:31]([CH3:33])[N:32]=4)=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:14]=2)=[CH:45][N:44]=[CH:43]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 774HistamineHCID 8471TriethylamineHCID 866396601-(4-Methylpiperazin-1-yl)-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)ethanone dihydrochloride

Product 1

HCID 86639662N-(2-(1H-imidazol-5-yl)ethyl)-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamide dihydrochlorideYield 86.9%

Procedure

2-(3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetic acid trifluoroacetate (prepared according to Example 27; 70 mg, 0.14 mmol), triethylamine (0.10 mL, 0.72 mmol) ethyl chloroformate (0.035 mL, 0.36 mmol) and 2-(1H-imidazol-5-yl)ethanamine (80 mg, 0.72 mmol) were reacted according to the method of Example 29 to provide N-(2-(1H-imidazol-5-yl)ethyl)-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetamide dihydrochloride (32.7 mg, 40.0% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 9.02 (d, 1H), 8.39 (t, 1H), 8.00 (dd, 1H), 7.66 (d, 1H), 7.40 (s, 1H), 7.30 (m, 2H), 7.19 (d, 1H), 7.16 (dd, 1H), 6.93 (s, 1H), 6.88 (dd, 1H), 5.33 (s, 2H), 4.52 (s, 2H), 3.45 (q, 2H), 2.86 (t, 2H), 2.35 (s, 3H). Mass spectrum (apci) m/z=465.2 (M+H-2HCl).

Sources & evidence

ORD record
ord-378ca6377eeb4f05970a0c37047bc570
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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