Hydrochloric Acid → N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-morpholin-4-yl-isonicotinamide

HRID 1582135Notes

Reaction equation

HRID 1582135 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:26])[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:15]=3)[S:11][C:7]=2[C:6]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:5][CH:4]=1.Cl.[C:34](OC(=O)C)(=[O:36])[CH3:35].C(=O)(O)[O-].[Na+]>C1COCC1.O.C(N(CC)CC)C>[C:34]([N:30]1[CH2:31][CH2:32][CH:27]([C:6]2[C:7]3[S:11][C:10]([NH:12][C:13](=[O:26])[C:14]4[CH:19]=[CH:18][N:17]=[C:16]([N:20]5[CH2:21][CH2:22][O:23][CH2:24][CH2:25]5)[CH:15]=4)=[N:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:28][CH2:29]1)(=[O:36])[CH3:35]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22719530N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-morpholin-4-yl-isonicotinamide

Product 1

HCID 10174399N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-morpholin-4-yl-isonicotinamideYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.05 g (0.095 mMol) N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-morpholin-4-yl-isonicotinamide 1:2 hydrochloride in 3 ml THF were added 0.029 ml triethyl amine. At 0° C. 0.011 ml (0.11 mMol) acetic anhydride was added dropwise and stirred for 1 h. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 10 ml water were added. This was extracted three times with 15 ml ethyl acetate, the combined organic phase were dried over sodium sulfate and evaporated to dryness in vacuo. One obtained 0.031 g (66%) N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-morpholin-4-yl-isonicotinamide as a white solid. F.p.: 231-233° C.

Workup

  1. customAt 0° C
  2. additionwere added
  3. extractionThis was extracted three times with 15 ml ethyl acetate
  4. dry with materialthe combined organic phase were dried over sodium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8d7ec44fa9754cd09ccf3ed83ccc2cae
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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