Sodium Hydroxide → HCID 22337610, compound

HRID 586077Notes

Reaction equation

HRID 586077 reaction equation
[CH:1]12[N:8]([C:9]3[CH:32]=[CH:31][C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]4[CH:26]=[CH:25][CH:24]=[C:23]5[C:19]=4[CH:20]=[N:21][N:22]5C(OC)=O)=[O:16])=[C:11]([Cl:33])[CH:10]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[OH-].[Na+]>CO>[CH:5]12[N:8]([C:9]3[CH:32]=[CH:31][C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]4[CH:26]=[CH:25][CH:24]=[C:23]5[C:19]=4[CH:20]=[N:21][NH:22]5)=[O:16])=[C:11]([Cl:33])[CH:10]=3)[CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22337663HCID 22337663, compound

Product 1

HCID 22337610HCID 22337610, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 4-[({[4-(8-azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzyl]amino}carbonyl)amino]-1H-indazole-1-carboxylate (803 mg, 1.72 mmol) in methanol (40 mL) was treated with 1.2N NaOH in MeOH (20 mL). After stirring for 30 minutes, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The separated aqueous phase was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (7% to 10% MeOH/CH2Cl2) to provide the title compound as a solid. The obtained solid was treated with ethanolic HCl followed by precipitation with diethyl ether to provide the hydrochloride salt. 1H NMR (300 MHz, DMSO-d6) δ 8.91 (s, 1H), 8.16 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.27 (d, 1H, J=8.5 Hz), 7.19 (t, 1H, J=8.1 Hz), 7.05 (d, 1H, J=8.5 Hz), 6.87 (m, 2H), 6.79 (m, 1H), 4.29 (m, 2H), 4.21 (m, 2H), 2.05-1.65 (m, 7H), 1.40 (m, 1H), 1.26 (m, 2H); MS (ESI) 410 (M+H)+; Anal. Calcd for C22H24ClN5O.1.6HCl: C, 56.43; H, 5.51; N, 14.96. Found: C, 56.30; H, 5.29; N, 14.81.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  3. extractionThe separated aqueous phase was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (7% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e4f13616644f41969c403bc8af05e0c9
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

Loading…