Hydrochloric Acid → 4-Chloro-N-[2-(7H-pyrrolo[2,3-d]pyrimidine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 1363059Notes

Reaction equation

HRID 1363059 reaction equation
COCN[C:5]([C:7]1[C:12]([N:13]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=2)(=[O:19])=[O:18])COC)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].I[C:32]1[C:33]2[CH:40]=[CH:39][N:38](COCC[Si](C)(C)C)[C:34]=2[N:35]=[CH:36][N:37]=1.CO.Cl>C1COCC1.C([Mg]Cl)(C)C>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([NH:13][C:12]2[C:7]([C:5]([C:32]3[C:33]4[CH:40]=[CH:39][NH:38][C:34]=4[N:35]=[CH:36][N:37]=3)=[O:6])=[N:8][CH:9]=[CH:10][CH:11]=2)(=[O:18])=[O:19])=[CH:21][C:22]=1[C:27]([F:29])([F:28])[F:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 578708034-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidineHCID 666022973-[(4-Chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid methoxymethyl-amide

Product 1

HCID 251710284-Chloro-N-[2-(7H-pyrrolo[2,3-d]pyrimidine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418918HCID 178418918, compoundSolvent

Procedure

Prepared from 248 mg (0.53 mmol) of 3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid methoxymethyl-amide, 239 mg (0.58 mmol) of 90% 4-iodo-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine dissolved in 2 mL THF with 0.32 mL of 2 M isopropylmagnesium chloride solution in THF added. All of the resulting intermediate ketone was used in the second step with 4 mL methanol and 4 mL 6N hydrochloric acid mixture to give after purification 29 mg of the final product as a yellow solid.

Workup

  1. additionadded
  2. customto give
  3. customafter purification 29 mg of the final product as a yellow solid

Sources & evidence

ORD record
ord-f54bbab366a24c50ae39196f691b8d61
Source dataset
uspto-grants-2011_02
Patent number
US07884110B2

Reaction notes

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