4-Methoxyphenoxyacetic acid → 1-(4-(5-Amino-2-(4-fluorophenethyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl)-2-(4-methoxyphenoxy)ethanone

HRID 1396704Notes

Reaction equation

HRID 1396704 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH2:7][C:8]2[S:9][C:10]3[N:11]=[C:12]([NH2:21])[N:13]=[C:14](S(C)(=O)=O)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32]([OH:34])=O)=[CH:28][CH:27]=1.CN(C(O[N:45]1N=[N:52][C:47]2C=CC=C[C:46]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:59][CH2:60]N(C(C)C)C(C)C>CN(C=O)C.O>[NH2:21][C:12]1[N:13]=[C:14]([N:45]2[CH2:46][CH2:47][N:52]([C:32](=[O:34])[CH2:31][O:30][C:29]3[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:36][CH:35]=3)[CH2:60][CH2:59]2)[C:15]2[N:16]=[C:8]([CH2:7][CH2:6][C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=3)[S:9][C:10]=2[N:11]=1

Participants

7

Reactant 4

HCID 746494-Methoxyphenoxyacetic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 509418672-(4-Fluorophenethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine

Product 1

HCID 469165231-(4-(5-Amino-2-(4-fluorophenethyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl)-2-(4-methoxyphenoxy)ethanoneYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine (40 mg, 0.11 mmol) and 4-methoxyphenoxyacetic acid (30 mg, 0.17 mmol) in DMF (2 ml) was added TBTU (N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate, 54 mg, 0.17 mmol), followed by DIPEA (29 μl, 0.17 mmol. The reaction mixture was stirred at room temperature for 3 hours. The mixture was diluted with water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over Na2SO4. After removing the solvents under reduced pressure, the crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 40:1), yielding the title compound as a white solid (40 mg, 69%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvents under reduced pressure
  5. customthe crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 40:1)

Sources & evidence

ORD record
ord-2c7b59be7b4d4ab1a739df103bd2f660
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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