Dichloromethane → HCID 50995469, compound

HRID 1772820Notes

Reaction equation

HRID 1772820 reaction equation
[N:1]1([CH2:7][CH:8]([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[CH:24]=[CH:23][N:22](COCC[Si](C)(C)C)[C:18]=4[N:19]=[CH:20][N:21]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.ClCCl.C(O)(C(F)(F)[F:48])=O>CO>[N:19]1[C:18]2[NH:22][CH:23]=[CH:24][C:17]=2[C:16]([C:14]2[CH:13]=[N:12][N:11]([CH:8]([CH2:9][CH3:10])[CH2:7][N:1]3[CH2:6][CH2:5][N:4]([C:33]([C:34]4[CH:39]=[CH:38][C:37]([F:48])=[CH:36][CH:35]=4)=[O:40])[CH2:3][CH2:2]3)[CH:15]=2)=[N:21][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 7412Benzoyl chlorideHCID 58181010HCID 58181010, compound

Product 1

HCID 50995469HCID 50995469, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-{1-[1-(piperazin-1-ylmethyl)propyl]-1H-pyrazol-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (0.010 g, 0.022 mmol, from step 4 in example 1) and benzoyl chloride, 4-fluoro-(3.4 uL, 0.028 mmol) in dichloromethane (1 mL, 20 mmol) was stirred for 2 hour. 1 mL TFA was added. After 1 hour, the solvent was evaporated by rotary evaporation to give a glass which was stirred in 1 mL MeOH and 50 microL EDA for 2 hours. The reaction was purified by LCMS (pH 10) to give 3.1 mg white solid (52% yield). 1H NMR (400 MHz, DMSO): δ 12.0 (1H, br); 8.62 (1H, s); 8.599 (1H, s); 8.22 (1H, s); 7.55 (1H, m); 7.18 (1H, m); 6.95 (1H, d); 6.91 (1H, d); 4.4 (1H, m); 3.43 (2H, br); 3.18 (2H, br); 2.82 (1H, m); 2.61 (1H, m); 2.47 (2H, br); 2.24 (2H, br); 1.78 (2H, m); 0.65 (3H, t). LCMS (M+1); 448.

Workup

  1. customthe solvent was evaporated by rotary evaporation
  2. customto give a glass which
  3. wait50 microL EDA for 2 hours
  4. customThe reaction was purified by LCMS (pH 10)

Sources & evidence

ORD record
ord-8d49ea92e1ed4d3d823a2afeb0931846
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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