Lithium hydroxide, monohydrate → HCID 67467334, compound

HRID 1476413Notes

Reaction equation

HRID 1476413 reaction equation
[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[C:15]4[CH:21]=[CH:20][NH:19][C:16]4=[N:17][CH:18]=3)[CH:9]=[C:8]([C:22]([O:24]C)=[O:23])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].O[Li].O>>[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[C:15]4[CH:21]=[CH:20][NH:19][C:16]4=[N:17][CH:18]=3)[CH:9]=[C:8]([C:22]([OH:24])=[O:23])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67467136Methyl 1-isopropyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxylate

Product 1

HCID 67467334HCID 67467334, compound

Conditions

Temperature
80 °C

Procedure

The title compound was prepared in the same manner as described for example 35 (step b) from methyl 1-isopropyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxylate 1 (0.6 g, 1.79 mmol) and LiOH.H2O (0.22 g, 5.37 mmol) wherein the mixture was heated at 80° C. for 5 h. The product was collected as an off-white solid (0.5 g, 87.7%). 1H NMR (DMSO-d6, 400 MHz): δ 1.530 (d, J=6.4 Hz, 6H), 5.199-5.265 (m, 1H), 6.552 (d, J=1.6 Hz, 1H), 7.550 (t, J=2.4 Hz, 1H), 8.11 (s, 1H), 8.328 (s, 1H), 8.383 (d, J=1.6 Hz, 1H), 8.401 (s, 1H), 8.671 (d, J=1.6 Hz, 1H), 11.77 (brs, 1H). LCMS (ES+) m/z: 321.24.

Workup

  1. customThe product was collected as an off-white solid (0.5 g, 87.7%)

Sources & evidence

ORD record
ord-7e32270ceb1549d9a053a40f5359432c
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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