Sodium Hydroxide → HCID 68291658, compound

HRID 1507927Notes

Reaction equation

HRID 1507927 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:11]=[N:10][N:9]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=[C:8]2[C:7]=1[NH:21][C@@H:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23]([O:25]C)=[O:24])(=[O:5])[NH2:4]>CO.C1COCC1>[C:3]([C:6]1[CH:11]=[N:10][N:9]2[CH:12]=[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:14]=[C:8]2[C:7]=1[NH:21][C@@H:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23]([OH:25])=[O:24])(=[O:5])[NH2:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68291852HCID 68291852, compound

Product 1

HCID 68291658HCID 68291658, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (11.200 ml, 11.20 mmol) added in one portion to a heterogeneous mixture of (S)-methyl 2-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)-2-phenylacetate (Example 121, 900 mg, 2.248 mmol) in MeOH (30 ml) and THF (15 ml). The reaction was allowed to stir at rt for ca. 2.5 hrs before removing the solvent in vacuo and cooling the flask in an ice bath. 1N aq. HCl was added and the yellow precipitate was then filtered and allowed to dry overnight. This afforded the title compound (915 mg, 100%) as a pale yellow solid. HPLC (condition B): retention time=0.87 min. LCMS (condition B): MH+ m/z 387.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.38 (1 H, d, J=7.04 Hz), 8.23 (1 H, s), 8.10 (1 H, d, J=1.54 Hz), 7.66 (2 H, d, J=7.26 Hz), 7.55 (2 H, d, J=7.48 Hz), 7.36 (5 H, q, J=7.92 Hz), 7.12-7.29 (4 H, m), 5.93 (1 H, br. s.).

Workup

  1. custombefore removing the solvent in vacuo
  2. temperaturecooling the flask in an ice bath
  3. addition1N aq. HCl was added
  4. filtrationthe yellow precipitate was then filtered
  5. customto dry overnight

Sources & evidence

ORD record
ord-98b2c2cd47af4110817aa468cb576507
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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