Triethylamine → 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(3-morpholinopropyl)benzamide hydrochloride

HRID 910997Notes

Reaction equation

HRID 910997 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)[CH:14]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:39][CH2:40][CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>CN(C=O)C>[ClH:2].[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:39][CH2:40][CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)=[O:9])=[CH:5][C:4]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 61055N-(3-Aminopropyl)morpholineHCID 248266634-Chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride

Product 1

HCID 248266674-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(3-morpholinopropyl)benzamide hydrochlorideYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following procedure of Example 83, 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride (0.100 g, 0.2511 mmol), triethylamine (0.1016 g, 1.004 mmol), (DMF (3 mL), ethyl carbonochloridate (0.02641 mL, 0.2762 mmol) and 4-(3-aminopropyl)morpholine (0.07242 g, 0.5022 mmol) were reacted to afford 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)-N-(3-morpholinopropyl)benzamide hydrochloride (0.030 g, 20.50% yield) as off white solid. 1H NMR (DMSO) δ 11.20 (bs, 1H), 10.37 (bs, 1H), 8.83 (t, 1H), 8.23 (d, 1H), 7.87 (dd, 1H), 7.84 (d, 1H), 7.82 (d, 1H), 6.58 (m, 2H), 6.55 (d, 1H), 3.94 (d, 2H), 3.72 (t, 2H), 3.40 (d, 2H), 3.32 (q, 2H), 3.12 (m, 2H), 3.03 (m, 2H), 2.21 (d, 3H), 1.93 (m, 2H); Mass spectrum (esi) m/z=488 (100) (M+H—HCl).

Sources & evidence

ORD record
ord-298e0bbf80f544f99694bebdec10accf
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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