Benzo(d)thiazol-2-amine → HCID 58996939, compound

HRID 1592571Notes

Reaction equation

HRID 1592571 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].NC1[S:15][C:16]2C=C[CH:20]=[CH:19][C:17]=2N=1.CCN(C(C)C)C(C)C.[CH3:32][C:33]1[C:34]([CH2:39][N:40]([CH2:47][C:48]2[C:53]([CH3:54])=[CH:52][CH:51]=[CH:50][N:49]=2)[CH:41]2[CH2:46]CNCC2)=[N:35][CH:36]=[CH:37][CH:38]=1>C(Cl)Cl.CN(C=O)C>[S:15]1[C:16]2[CH:17]=[CH:19][CH:20]=[CH:12][C:11]=2[N:10]=[C:9]1[NH:8][C:1]([N:3]1[CH2:4][CH2:46][CH:41]([N:40]([CH2:39][C:34]2[C:33]([CH3:32])=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:47][C:48]2[C:53]([CH3:54])=[CH:52][CH:51]=[CH:50][N:49]=2)[CH2:6][CH2:7]1)=[O:2]

Participants

7

Reactant 4

HCID 8706Benzo(d)thiazol-2-amineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 58996965Bis-(3-methyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 58996939HCID 58996939, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1,1′-carbonyldiimidazole (86.2 mg, 0.531 mmol), 2-aminobenzothiazole (72.6 mg, 0.483 mmol), and DIPEA (0.17 mL, 0.97 mmol) in CH2Cl2 (5 mL) and DMF (3 mL) was stirred at room temperature for 4 h. The mixture was concentrated to a minimum volume, diluted with DMF (3 mL), and COMPOUND 249 (150 mg, 0.482 mmol) was added and stirred at 60° C. for 16 hours. The solution was concentrated to dryness, treated with saturated aqueous NaHCO3 (30 mL) and H2O (10 mL), and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification of the crude material by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 90:5:5) provided COMPOUND 291 (107 mg, 45%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated to a minimum volume
  2. additionwas added
  3. concentrationThe solution was concentrated to dryness
  4. additiontreated with saturated aqueous NaHCO3 (30 mL) and H2O (10 mL)
  5. extractionextracted with CH2Cl2 (3×15 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the crude material by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 90:5:5)

Sources & evidence

ORD record
ord-979db21c6de54e309a86f3242afc003e
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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