Diisopropylethylamine → HCID 71612386, compound

HRID 1774548Notes

Reaction equation

HRID 1774548 reaction equation
[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:15]([F:16])=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[CH:12][C:11]=3[F:20])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[C:33]([C:34]([OH:36])=O)=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:37][CH3:38])=[CH:23][N:22]=3)[C:5]=2[CH3:39])[CH2:3][CH2:2]1.[NH2:40][CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C.O>[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:11]([F:20])=[CH:12][C:13]([O:17][CH2:18][CH3:19])=[CH:14][C:15]=3[F:16])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[C:33]([C:34]([NH:40][CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])=[O:36])=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:37][CH3:38])=[CH:23][N:22]=3)[C:5]=2[CH3:39])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 43405612-(Methylsulfonyl)ethanamineHCID 71612269HCID 71612269, compound

Product 1

HCID 71612386HCID 71612386, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 147 mg 4-({2-[5-cyclopropyl-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazol-3-yl]-5-methoxypyrimidin-4-yl}amino)nicotinic acid 2-11-1 (0.27 mmol, 1.0 eq) and 67.5 mg 2-aminoethylmethyl sulfone (0.55 mmol, 2.0 eq) in 2.1 mL DMF were added 191 μL N,N-diisopropylethylamine (1.10 mmol, 4.0 eq) and 157 mg (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.30 mmol, 1.1 eq). The resulting solution was stirred over night at rt and afterwards diluted with water. The precipitate was collected by filtration, washed with water and dried. The crude product was purified by preparative HPLC yielding 40 mg of analytically pure target compound (62 μmol, 22%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-93fde59e69554cf5b2ec5334311da551
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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