4-Penten-1-OL → 2-(4-Chlorophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)(pent-4-en-1-yl)amino]-2H-indazole-3-carboxamide

HRID 63538

Reaction equation

HRID 63538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH2:29](O)[CH2:30][CH2:31][CH:32]=[CH2:33]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:33][CH2:32][CH2:31][CH:30]=[CH2:29])[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 131814-Penten-1-OLHCID 56963169HCID 56963169, compound

Product 1

HCID 866990012-(4-Chlorophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)(pent-4-en-1-yl)amino]-2H-indazole-3-carboxamideYield 69%

Procedure

Synthesized under alkylation conditions by reacting 2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide (200 mg, 0.48 mmol) with 4-penten-1-ol (0.1 mL). Work up and purification afforded (i) (161 mg, 69%). 1H NMR (400 MHz, CDCl3) δ 7.72 (d, J=0.5 Hz, 1H), 7.56-7.48 (m, 4H), 7.37 (s, 1H), 5.88-5.66 (m, 2H), 5.03-4.93 (m, 2H), 3.73 (t, J=7.8 Hz, 2H), 3.05 (s, 3H), 3.01 (d, J=4.9 Hz, 3H), 2.49-2.37 (m, 1H), 2.15-2.05 (m, 2H), 1.85-1.62 (m, 2H), 1.15-1.04 (m, 2H), 1.04-0.93 (m, 1H), 0.67-0.52 (m, 1H). ESI-MS m/z calculated for [M+H]+: 487.2. found: 487.1.

Workup

  1. customSynthesized under alkylation conditions
  2. custompurification

Sources & evidence

ORD record
ord-d62f29db5c81499eb8468ae3e8c77e76
Source dataset
uspto-grants-2016_09
Patent number
US09447080B2

Linked notes

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