Pyridine → HCID 178511264, compound

HRID 40989Notes

Reaction equation

HRID 40989 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-f48b3aa2cbff4cd390418e7dfd1bbbe4
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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