Pyridine → HCID 178511264, compound

HRID 1843565Notes

Reaction equation

HRID 1843565 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([C@@H:21]4[CH2:26][CH2:25][C@H:24]([CH:27]=[N:28]O)[CH2:23][CH2:22]4)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.N1C=CC=CC=1.C1(S(Cl)(=O)=O)C=CC=CC=1>CC#N.O>[N:12]1[C:11]2[NH:7][CH:8]=[CH:9][C:10]=2[C:15]([C:16]2[CH:17]=[N:18][N:19]([C@@H:21]3[CH2:22][CH2:23][C@H:24]([C:27]#[N:28])[CH2:25][CH2:26]3)[CH:20]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 178504219HCID 178504219, compound

Product 1

HCID 178511264HCID 178511264, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

[A] cis-4-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclohexanecarbaldehyde oxime (11.0 mg, 0.0000250 mol) was dissolved in pyridine (0.25 mL, 0.0031 mol), and benzenesulfonyl chloride (10.0 μL, 0.0000784 mol) was added and the resulting mixture was stirred at rt. After stirring 15 h, LCMS analysis showed formation of the product, M+H 423. The product was isolated by prep HPLCMS using a 19 mm×100 mm C18 column; 45% CH3CN—H2O (0.1% NH4OH), 1 min, to 75% at 6 min; 30 mL/min; detector set at m/z 423; retention time, 4.8 min. The eluent was concentrated using a rotary evaporator to give 8 mg of the desired product.

Workup

  1. stirringAfter stirring 15 h
  2. customThe product was isolated by prep HPLCMS
  3. customretention time, 4.8 min
  4. concentrationThe eluent was concentrated
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-c3fb5e76e4ae4c30ad705049c8722a77
Source dataset
uspto-grants-2015_02
Patent number
US08946245B2

Reaction notes

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