Potassium Sodium Tartrate → HCID 58266664, compound

HRID 1506012Notes

Reaction equation

HRID 1506012 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:19]=[CH:18][C:17]2[NH:16][C:15]3[N:20]=[CH:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30][N:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[CH:26][CH:25]=4)=[CH:23][C:14]=3[C:13]=2[CH:12]=1)=O.[Cl-].[NH4+].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.O.C(Cl)Cl.CO>[N:31]1([CH2:30][C:27]2[CH:28]=[CH:29][C:24]([C:22]3[CH:21]=[N:20][C:15]4[NH:16][C:17]5[CH:18]=[N:19][C:11]([CH2:9][OH:8])=[CH:12][C:13]=5[C:14]=4[CH:23]=3)=[CH:25][CH:26]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

8

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydride2×HCID 67027520HCID 67027520, compound

Product 1

HCID 58266664HCID 58266664, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 21226129Dichloromethane methanolSolvent

Procedure

A 1M solution of lithium aluminum hydride in THF (1.2 mL, 1.2 mmol) was slowly added to a suspension of 3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (48.0 mg, 0.120 mmol) in THF at 0° C. The mixture was slowly warmed to ambient temperature. A further portion of 1M solution of lithium aluminum hydride in THF (1.2 mL, 1.2 mmol) was added slowly to the bright orange-yellow, homogeneous mixture at ambient temperature. After 1 h, the mixture was treated with aqueous ammonium chloride, and diluted with water and 50% DCM/methanol. The resulting mixture was treated with Rochelle's salt and allowed to stir vigorously for 2 h. The solids were removed by filtration, and the filtrate layers were separated. The aqueous phase was extracted with 20% methanol in DCM and the combined organic phase concentrated in vacuo. The residue was dissolved in DMSO and purified by preparative HPLC (2-60% MeCN/water modified with 0.1% ammonium hydroxide) to provide a light-yellow solid (7.1 mg, 16%). 1H NMR (DMSO-D6, 400 MHz): 12.10 (s, 1H), 9.02 (m, 1H), 8.90 (m, 1H), 8.82 (m, 1H), 8.28 (m, 1H), 7.79 (m, 2H), 7.46 (m, 2H), 5.40 (t, J=5.7 Hz, 1H), 4.74 (d, J=5.6 Hz, 2H), 3.59-3.41 (m, 2H), 2.38 (m, 4H), 1.54 (m, 4H), 1.42 (m, 2H). LCMS (Method D): RT=4.48 min, M+H+=373.

Workup

  1. customThe solids were removed by filtration
  2. customthe filtrate layers were separated
  3. extractionThe aqueous phase was extracted with 20% methanol in DCM
  4. concentrationthe combined organic phase concentrated in vacuo
  5. dissolutionThe residue was dissolved in DMSO
  6. custompurified by preparative HPLC (2-60% MeCN/water modified with 0.1% ammonium hydroxide)

Sources & evidence

ORD record
ord-2a83b82e7f3d4c07843cda74f26f954e
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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