Triethylamine → HCID 178513963, compound

HRID 2274824Notes

Reaction equation

HRID 2274824 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([C@@H:25]4[CH2:28][C@H:27]([C:29](O)=[O:30])[CH2:26]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.CC[N:34](CC)CC.[NH4+].[Cl-].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([C@@H:25]4[CH2:26][C@H:27]([C:29]([NH2:34])=[O:30])[CH2:28]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178525796HCID 178525796, compound2×

Product 1

HCID 178513963HCID 178513963, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of cis-3-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)cyclobutanecarboxylic acid (Intermediate 36; 100 mg; 0.23 mmol), Et3N (0.13 mL; 0.93 mmol), NH4Cl (24 mg; 0.45 mmol) and HATU (173 mg; 0.45 mmol) in THF (5 mL) was stirred for 1 hour. The reaction mixture was added water (20 mL) and extracted with EtOAc (50 mL×2). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to afford 98 mg (98%) of the title compound as a white solid, which was used directly without further purification.

Workup

  1. extractionextracted with EtOAc (50 mL×2)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d01ead872024635aa98070aa5561c8d
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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