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

HRID 251152Notes

Reaction equation

HRID 251152 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. 1H NMR (CDCl3) δ 1.57-1.76 (m, 2H), 1.94 (d, 2H, J=11.7 Hz), 2.05 (s, 6H), 2.62-2.84 (m, 3H), 3.79 (s, 4H), 4.26 (d, 2H, J=11.7 Hz), 7.02-7.11 (m, 2H), 7.16-7.27 (m, 1H), 7.29-7.40 (m, 3H), 7.58 (d, 1H, J=7.8 Hz), 7.74 (d, 1H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz), 9.91 (br s, 1H); 13C NMR (CDCl3) 18.36, 27.44, 44.89, 54.89, 57.59, 119.09, 121.83, 122.84, 123.55, 126.34, 131.83, 133.77, 138.46, 146.27, 147.01, 154.75, 157.37, 163.38; ES-MS m/z 509 (M+Na). Anal. Calcd. for C27H30N6OS.1.0 CH2Cl2: C, 58.84; H, 5.64; N, 14.70. Found: C, 58.69; H, 5.57; N, 14.82.

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-5f7a8eb62bf249b8b4752b81a687b36e
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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