1H-1,2,4-Triazole → HCID 59331603, compound

HRID 1882115Notes

Reaction equation

HRID 1882115 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32]O)=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(P(CCCC)CCCC)CCC.[NH:47]1[CH:51]=[N:50][CH:49]=[N:48]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[CH:27]=[CH:28][C:29]([CH2:32][N:47]5[CH:51]=[N:50][CH:49]=[N:48]5)=[CH:30][N:31]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 92571H-1,2,4-Triazole2×HCID 13831Tributylphosphine2×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 59331365HCID 59331365, compound

Product 1

HCID 59331603HCID 59331603, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [6-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridin-3-yl]methanol (430 mg), tributylphosphine (280 mg), 1,2,4-triazole (76 mg) and tetrahydrofuran (30 mL) was added 1,1′-(azodicarbonyl)dipiperidine (350 mg) at room temperature, and the mixture was stirred at room temperature for 15 hr. To the mixture were added 1,2,4-triazole (76 mg) and tributylphosphine (280 mg), 1,1′-(azodicarbonyl)dipiperidine (350 mg) was further added at room temperature, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated, ethyl acetate was added to the residue, and the insoluble material was filtered off. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography to give the title compound as a crude product from a fraction eluted with ethyl acetate-methanol (100:0-90:10, volume ratio), and the crude product was subjected to preparative HPLC to give the title compound as an oil. The oil was crystallized from acetonitrile-diethyl ether, and further recrystallized from acetone-hexane to give the title compound (38 mg, yield 8%) as colorless crystals. MS: 518 (MH+). melting point 152-153° C.

Workup

  1. additionwas further added at room temperature
  2. stirringthe mixture was stirred at room temperature for 4 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. filtrationthe insoluble material was filtered off
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c8b37294dd4c4962ac5f877a6fc3d0b8
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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