Sodium Bicarbonate → HCID 59626746, compound

HRID 2400374Notes

Reaction equation

HRID 2400374 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[C:19]([CH2:28][NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[C:20]2[C:24](=[C:25]([Cl:27])[CH:26]=1)[NH:23][N:22]=[CH:21]2)[C:13]([O:15]C)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:27][C:25]1[C:24]2[NH:23][N:22]=[CH:21][C:20]=2[C:19]2[CH2:28][N:29]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[C:13](=[O:15])[CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:17][C:18]=2[CH:26]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59626688HCID 59626688, compound

Product 1

HCID 59626746HCID 59626746, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of Methyl 2-{[(benzyloxy)carbonyl]amino}-3-(7-chloro-4-{[(4-methoxybenzyl)amino]methyl}-1H-indazol-5-yl)propanoate from Step A in toluene (100 mL) was heated at reflux for 3 hours and then cooled to room temperature. The reaction mix was poured into a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with Ethyl acetate (2×200 mL). The combined organic extracts were washed once with brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure. The resulting solid was swished once with a 1:1 mix of ethylacetate/hexane and the solid collected by filtration to give 3.1 g of the title compound to give the title compound. MS: m/z 505 (M+1).

Workup

  1. temperatureat reflux for 3 hours
  2. additionThe reaction mix
  3. extractionthe mixture was extracted with Ethyl acetate (2×200 mL)
  4. washThe combined organic extracts were washed once with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. additionmix of ethylacetate/hexane
  9. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-083a2625ae25469b8deaf73d6da73376
Source dataset
uspto-grants-2014_08
Patent number
US08796260B2

Reaction notes

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