HCID 59733723, compound → HCID 59733718, compound

HRID 132111Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([C:11]2([NH2:30])[CH2:19][CH2:18][C:17]3[C:13](=[CH:14][N:15]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[N:16]=3)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:33]=[C:34]([CH2:39][CH2:40][CH:41]2[CH2:43][O:42]2)[CH:35]=[C:36]([F:38])[CH:37]=1>C(O)(C)C>[C:1]([C:5]1[CH:6]=[C:7]([C:11]2([NH:30][CH2:43][CH:41]([OH:42])[CH2:40][CH2:39][C:34]3[CH:35]=[C:36]([F:38])[CH:37]=[C:32]([F:31])[CH:33]=3)[CH2:19][CH2:18][C:17]3[C:13](=[CH:14][N:15]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[N:16]=3)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a sealed tube was added a solution of 5-(3-tert-butyl-phenyl)-2-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (0.41 g, 1.0 mmol) in isopropyl alcohol followed by 2-[2-(3,5-difluoro-phenyl)-ethyl]-oxirane (0.18 g, 1.0 mmol). The reaction was heated at 50° C. overnight and no product was formed. After heating at 100° C. for an additional 3.5 h the reaction was complete. The reaction mixture was concentrated and the crude product was purified by flash chromatography, eluting with 3% methanol in CHCl3 to afford 0.25 g (0.41 mmol, 42%) of 1-[5-(3-tert-butyl-phenyl)-2-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamino]-4-(3,5-difluoro-phenyl)-butan-2-ol: retention time (min)=2.15, method [1]. MS (ESI) 608.4 (M+H).

Workup

customno product was formed
temperatureAfter heating at 100° C. for an additional 3.5 h the reaction
concentrationThe reaction mixture was concentrated
customthe crude product was purified by flash chromatography
washeluting with 3% methanol in CHCl3

Sources & evidence

ORD record: ord-bcf89a5076ed47f687a002bd3808e5ad
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07385085B2

Reaction notes

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