Benzo(d)thiazol-2-amine → HCID 58997213, compound

HRID 251167Notes

Reaction equation

HRID 251167 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[CH3:23][C:24]1[C:25]([CH2:31][N:32]([CH2:39][C:40]2[C:45]([CH:46]([CH3:48])[CH3:47])=[CH:44][CH:43]=[CH:42][N:41]=2)[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=1>C(Cl)Cl>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[NH:13][C:1]([N:36]1[CH2:37][CH2:38][CH:33]([N:32]([CH2:31][C:25]2[C:24]([CH3:23])=[CH:29][C:28]([CH3:30])=[CH:27][N:26]=2)[CH2:39][C:40]2[C:45]([CH:46]([CH3:48])[CH3:47])=[CH:44][CH:43]=[CH:42][N:41]=2)[CH2:34][CH2:35]1)=[O:2]

Participants

5

Reactant 3

HCID 8706Benzo(d)thiazol-2-amineHCID 682631,1'-CarbonyldiimidazoleHCID 58997074(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 58997213HCID 58997213, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1′-carbonyldiimidazole (125 mg, 0.77 mmol) in CH2Cl2 (5 mL) was added 2-aminobenzothiazole (95 mg, 0.64 mmol). The resulting suspension was stirred for 2 h and then concentrated under reduced pressure. The residue was dissolved in CH3CN (5 mL) and was treated with (3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidine-4-yl-amine (112 mg, 0.32 mmol) and the reaction mixture was stirred at 60° C. overnight. Then the mixture was cooled and diluted with CH2Cl2/saturated NaHCO3 (1:1, 40 mL). The aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to afford a pink foam. Purification by radial chromatography on silica gel (2 mm plate; using CH2Cl2/MeOH/NH4OH; 50:1:1) afforded the product as a white solid (84 mg, 50%). 1H NMR (CDCl3) δ 0.91 (d, 6H, J=6.9 Hz), 1.60-1.72 (m, 2H), 1.91 (d, 2H, J=11.4 Hz), 2.14 (s, 3H), 2.27 (s, 3H), 2.68-2.80 (m, 4H), 3.74 (s, 2H), 3.81 (s, 2H), 4.24 (br s, 1H), 4.28 (br s, 1H), 7.13 (dd, 1H, J=7.8, 4.8 Hz), 7.148-7.24 (m, 2H), 7.35 (t, 1H, J=7.2 Hz), 7.48 (dd, 1H, J=7.8, 1.5 Hz), 7.58 (br d, 1H, J=8.1 Hz), 7.74 (br d, 1H, J=7.8 Hz), 8.18 (s, 1H), 8.31 (dd, 1H, J=4.5, 1.5 Hz). 13C NMR (CDCl3) δ 18.30, 18.47, 23.61, 27.41, 27.65, 44.94, 54.31, 57.18, 119.37, 121.81, 123.20, 123.58, 126.35319 132.04, 132.31, 133.18, 133.87, 139.07, 144.38, 146.11, 146.68, 147.39, 154.36, 156.18, 162.71. ES-MS m/z 529 [M+H]+. Anal. Calcd. for C30H36N6OS.0.1CH2Cl2: C, 67.30; H, 6.79; N, 15.64; S, 5.97. Found: C, 67.56; H, 6.86; N, 15.52; S, 5.89.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH3CN (5 mL)
  3. stirringthe reaction mixture was stirred at 60° C. overnight
  4. temperatureThen the mixture was cooled
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a pink foam
  10. customPurification by radial chromatography on silica gel (2 mm plate; using CH2Cl2/MeOH/NH4OH; 50:1:1)

Sources & evidence

ORD record
ord-e50c30918baa4d4883df3cc6426b6ae7
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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