Pyridine → HCID 66798088, compound

HRID 1397574Notes

Reaction equation

HRID 1397574 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][C@@H:13]([OH:15])[C@H:12]([NH:16][C:17]2[CH:22]=[C:21]([NH:23][C@@H:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[N:20]=[CH:19][N:18]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>C(Cl)Cl.O>[C:39]([O:15][C@@H:13]1[CH2:14][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH2:11][C@H:12]1[NH:16][C:17]1[CH:22]=[C:21]([NH:23][C@@H:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]2)[N:20]=[CH:19][N:18]=1)(=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 66797922HCID 66797922, compound

Product 1

HCID 66798088HCID 66798088, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2R,4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)cyclopentanol (0.193 g, 0.424 mmol), N,N-dimethylaminopyridine (4.7 mg, 0.039 mmol) and pyridine (0.281 mL, 3.48 mmol) in DCM (2.1 mL) was added acetic anhydride (0.044 mL, 0.46 mmol) and the mixture stirred overnight. The reaction was diluted with CH2CL2 (10 mL) and H2O (20 mL) then stirred for 10 m. The organic layer was separated and the aqueous layer was extracted with CH2CL2 and combined organics were washed with H2O. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to obtain the title compound. LC/MS: Rt=1.74 min, ES+ 498 (FA Standard).

Workup

  1. stirringthen stirred for 10 m
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2CL2
  4. washcombined organics were washed with H2O
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40e80c2b32384a85894ebc73ce6e02e8
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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