Water → HCID 59224897, compound

HRID 905646Notes

Reaction equation

HRID 905646 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])=[CH:30][N:29]=1)=[O:27])=[O:17])([CH3:14])([CH3:13])[CH3:12].O.C1C[O:46][CH2:45]C1>>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:1][C:45](=[O:46])[N:35]([CH2:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]([NH:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])=[O:27])=[N:29][CH:30]=1)[CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8706Benzo(d)thiazol-2-amineHCID 59225188HCID 59225188, compound

Product 1

HCID 59224897HCID 59224897, compound

Procedure

Under ice cooling, 2-amino-1,3-benzothiazole (100 mg, 0.60 mmol) was added to a solution of N,N′-carbonyldiimidazole (98 mg, 0.60 mmol) in THF (3.0 mL), and then the reaction mixture was stirred for 2 hours. N-(2-t-butoxycarbonylaminophenyl)-5-(3-dimethylaminopropylaminomethyl)pyridine-2-carboxylic acid amide (Reference Compound No. 5-1, 90 mg, 0.20 mmol) was added thereto, and then the reaction mixture was stirred at 60° C. for 3 hours. Water (30 mL) was added thereto, the whole was extracted with ethyl acetate (30 mL) twice, and then the organic layer was washed with water (30 mL) and brine (30 mL). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to give 220 mg of a mixture containing the title reference compound as a white amorphous product.

Workup

  1. addition5-1, 90 mg, 0.20 mmol) was added
  2. stirringthe reaction mixture was stirred at 60° C. for 3 hours
  3. extractionthe whole was extracted with ethyl acetate (30 mL) twice
  4. washthe organic layer was washed with water (30 mL) and brine (30 mL)
  5. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5955d527c788463996691d410ab90890
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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