Acetone → N-{2-[Methyl-(1-methyl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-4-(2-methyl-thiazol-4-yl)-benzamide

HRID 1175003Notes

Reaction equation

HRID 1175003 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[N:6]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:38][N:39]([CH:50]1[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]1)[C:40]1[O:41][C:42]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][C:43]=2[N:44]=1.CC(C)=O>CN(C=O)C>[CH3:38][N:39]([CH:50]1[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]1)[C:40]1[O:41][C:42]2[CH:48]=[CH:47][C:46]([NH:49][C:11](=[O:13])[C:10]3[CH:9]=[CH:8][C:7]([C:5]4[N:6]=[C:2]([CH3:1])[S:3][CH:4]=4)=[CH:15][CH:14]=3)=[CH:45][C:43]=2[N:44]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6549804-(2-Methyl-1,3-thiazol-4-yl)benzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59558009N2-Methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine

Product 1

HCID 57771736N-{2-[Methyl-(1-methyl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-4-(2-methyl-thiazol-4-yl)-benzamideYield 106.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-(2-methyl-1,3-thiazol-4-yl)benzoic acid (55 mg, 0.251 mmol), TBTU (74 mg, 0.232 mmol), and N2-Methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine (46 mg, 0.177 mmol) in DMF (1.0 mL) and shake at room temperature. Add acetone (2.0 mL) a put the mixture on an SCX cartridge (previously conditioned with MeoH). Wash with acetone (3×3.0 mL) non basic impurities and then with MeOH (3×3.0 mL). Eluting with a 2N solution of NH3 in MeOH (4.0 ml) and concentrate to afford the title compound (87 mg, 100%). LC/MS, RT=4.45 min., mass spectrum (m/z) found (M+H)+: 462.2. The material is dissolved in MeOH and treated with 2M HCl in ether (2.0 mL). Organic solvent is removed in vacuo and the resulting precipitate is collected to give 96 mg of the hydrochloride salt.

Workup

  1. customshake at room temperature
  2. washWash with acetone (3×3.0 mL) non basic impurities
  3. washEluting with a 2N solution of NH3 in MeOH (4.0 ml)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-63902d32004b456db71623fa85aacb8d
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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