Hydrochloric Acid → 2-(6-{[3-(morpholin-4-yl)propyl]aminocarbonyl}-benzothiazol-2(3H)-ylidene)-2-(4-trifluoromethyl-pyrimidin-2-yl)acetamide hydrochloride

HRID 1091671Notes

Reaction equation

HRID 1091671 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]2[NH:8][C:9](=[C:11]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=3)[C:12]([NH2:14])=[O:13])[S:10][C:6]=2[CH:5]=1)(O)=[O:2].C(N(CC)CC)C.CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.[N:54]1([CH2:60][CH2:61][CH2:62][NH2:63])[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1.[ClH:64]>C(#N)C.O1CCOCC1>[ClH:64].[N:54]1([CH2:60][CH2:61][CH2:62][NH:63][C:1]([C:4]2[CH:26]=[CH:25][C:7]3[NH:8][C:9](=[C:11]([C:15]4[N:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][N:16]=4)[C:12]([NH2:14])=[O:13])[S:10][C:6]=3[CH:5]=2)=[O:2])[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 665935492-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Product 1

HCID 665936002-(6-{[3-(morpholin-4-yl)propyl]aminocarbonyl}-benzothiazol-2(3H)-ylidene)-2-(4-trifluoromethyl-pyrimidin-2-yl)acetamide hydrochlorideYield 73%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a room temperature solution of 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (350 mg, 0.92 mmol) in acetonitrile (5 mL) was added triethylamine (250 μL, 1.79 mmol, 2 eq.), DEPBT (299 mg, 1.0 mmol, 1.1 eq.), and 3-(4-morpholinyl)-propan-1-amine (134 μL, 0.92 mmol, 1.0 eq.), and the mixture was stirred at room temperature until a yellow-brown precipitate formed. The precipitate was collected by filtration, washed with acetonitrile, and dried under vacuum to give a yellow solid. About 2 mL of 4.0 M hydrogen chloride in dioxane was added, and the mixture was stirred for 15 min and then concentrated under reduced pressure to give 2-(6-{[3-(morpholin-4-yl)propyl]aminocarbonyl}-benzothiazol-2(3H)-ylidene)-2-(4-trifluoromethyl-pyrimidin-2-yl)acetamide hydrochloride (340 mg, 73% yield) as a yellow solid.

Workup

  1. customformed
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with acetonitrile
  4. customdried under vacuum
  5. customto give a yellow solid
  6. stirringthe mixture was stirred for 15 min
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d738d64f1f64859ba969e036d23d961
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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