Triphenylphosphine → 3-{3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzyl}-5-trifluoromethyl-3H-benzothiazol-2-one

HRID 330801Notes

Reaction equation

HRID 330801 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9](=[O:11])[NH:8][C:7]=2[CH:12]=1.[CH3:15][N:16]([CH3:35])[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[N:23][C:24]([C:27]2[CH:28]=[C:29]([CH2:33]O)[CH:30]=[CH:31][CH:32]=2)=[N:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:35][N:16]([CH3:15])[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[N:25][C:24]([C:27]2[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=2)[CH2:33][N:8]2[C:7]3[CH:12]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=[CH:5][C:6]=3[S:10][C:9]2=[O:11])=[N:23][CH:22]=1

Participants

5

Reactant 4

HCID 11776Triphenylphosphine2×HCID 97268Di-tert-butyl azodicarboxylate2×HCID 132273405-(Trifluoromethyl)benzo[d]thiazol-2(3H)-oneHCID 59484942{3-[5-(3-Dimethylaminopropoxy)pyrimidin-2-yl]phenyl}methanol

Product 1

HCID 468466283-{3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzyl}-5-trifluoromethyl-3H-benzothiazol-2-one

Procedure

A suspension of 114 mg (0.52 mmol) of 5-trifluoromethyl-3H-benzothiazol-2-one, 150 mg (0.52 mmol) of {3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]phenyl}methanol and 261 mg (0.78 mmol) of polymer-bound triphenylphosphine (3mmol/g) is shaken at room temperature for 30 min. 178 mg (0.78 mmol) of di-tert-butyl azodicarboxylate are added to the suspension, and, after the mixture has been stirred at room temperature for 24 h, 50 mg (0.15 mmol) of polymer-bound triphenylphosphine (3 mmol/g) and 35 mg (0.15 mmol) of di-tert-butyl azodicarboxylate are again present and shaken at room temperature for 2 h. The reaction mixture is filtered, the filtrate is evaporated to dryness, and the residue is purified by means of preparative HPLC. The product is in the form of the trifluoroacetate; ESI: 489 (M+H); Rt.=2.81 min (method A);

Workup

  1. stirringafter the mixture has been stirred at room temperature for 24 h
  2. stirringshaken at room temperature for 2 h
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated to dryness
  5. customthe residue is purified by means of preparative HPLC
  6. custom=2.81 min (method A)

Sources & evidence

ORD record
ord-f937e100eef7407481c2c51dceb0527a
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

Loading…