(4-Chlorophenyl)acetic acid → HCID 66571607, compound

HRID 82082Notes

Reaction equation

HRID 82082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:12][C:13]1[N:14]=[CH:15][C:16]2[C:21]([C:22]([C:24]3[CH:25]=[N:26][CH:27]=[C:28]([NH2:30])[CH:29]=3)=[O:23])=[CH:20][N:19]([CH:31]([CH3:34])[CH2:32][OH:33])[C:17]=2[N:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[NH2:12][C:13]1[N:14]=[CH:15][C:16]2[C:21]([C:22]([C:24]3[CH:29]=[C:28]([NH:30][C:9](=[O:11])[CH2:8][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH:27]=[N:26][CH:25]=3)=[O:23])=[CH:20][N:19]([CH:31]([CH3:34])[CH2:32][OH:33])[C:17]=2[N:18]=1

Participants

6

Reactant 4

HCID 15880(4-Chlorophenyl)acetic acidHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70817362[2-amino-7-(2-hydroxy-1-methylethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl](5-aminopyridin-3-yl)methanone

Product 1

HCID 66571607HCID 66571607, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chlorophenylacetic acid (25 mg, 0.14 mmol) was added to [2-amino-7-(2-hydroxy-1-methylethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl](5-aminopyridin-3-yl)methanone (50 mg, 0.16 mmol) (see Preparation 57) and HATU (91 mg, 0.24 mmol) in pyridine (2 mL). The mixture was stirred at room temperature for 16 hours. Saturated aqueous sodium bicarbonate (5 mL) was added then extracted with ethyl acetate (3×5 mL). The combined organic phases were washed with brine (5 mL) then dried over sodium sulfate and evaporated in vacuo. The residue was purified by preparative TLC (95:5 DCM:MeOH) to afford the title compound as a yellow solid in 48% yield, 32 mg.

Workup

  1. extractionthen extracted with ethyl acetate (3×5 mL)
  2. washThe combined organic phases were washed with brine (5 mL)
  3. dry with materialthen dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative TLC (95:5 DCM:MeOH)

Sources & evidence

ORD record
ord-9b2db479ee5344e5a584c992f90e9324
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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