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

HRID 1054513Notes

Reaction equation

HRID 1054513 reaction equation
CON(C)[C:4]([C:6]1[C:11]([N:12]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=2)(=[O:18])=[O:17])COC)=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].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:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([NH:12][C:11]2[C:6]([C:4]([C:32]3[C:33]4[CH:40]=[CH:39][NH:38][C:34]=4[N:35]=[CH:36][N:37]=3)=[O:5])=[N:7][CH:8]=[CH:9][CH:10]=2)(=[O:18])=[O:17])=[CH:20][C:21]=1[C:26]([F:28])([F:27])[F:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 578708034-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidineHCID 578708053-[(4-Chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid methoxy-methyl-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 methoxy-methyl-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-51ec027f178d4a23aa59ef0a8a108793
Source dataset
uspto-grants-2016_07
Patent number
US09394307B2

Reaction notes

Loading…