Indazole-3-carboxylic acid → HCID 57841347, compound

HRID 733576Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][CH2:19][C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([C:43](O)=[O:44])=[N:35]1>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=3)[C:43]([C:36]3[C:37]4[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=4)[NH:34][N:35]=3)=[O:44])=[CH:32][CH:33]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 78250Indazole-3-carboxylic acid

HCID 57554567Methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}acetate

Product 1

HCID 57841347HCID 57841347, compound

Procedure

The titled compound was prepared following the procedure H using methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}acetate and 1H-indazole-3-carboxylic acid as a yellow oil (55%). 1H NMR (MeOD, 300 MHz) δ 8.05 (m, 1H), 7.17-7.56 (m, 13H), 6.88 (m, 2H), 5.06 (s, 1H), 5.02 (s, 1H), 4.68 (m, 4H), 3.76 (s, 3H), 2.62 (t, J=7.4 Hz, 2H), 1.60 (m, 2H), 1.34 (m, 2H), 0.94 (t, J=7.4 Hz, 3H). M− (ESI): 584.4; M+ (ESI): 5.86.3. HPLC, Rt: 5.49 min (Purity: 84.1%).

Sources & evidence

ORD record: ord-fc115e43fc7a4950b1f7bbf312ad4076
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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