Sodium Hydroxide → HCID 178433160, compound

HRID 2391003Notes

Reaction equation

HRID 2391003 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH:13]=O)[CH2:9][CH2:8]1)=[O:5].[CH3:23][C:24]1[S:28][C:27]([NH2:29])=[N:26][CH:25]=1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][NH:29][C:27]2[S:28][C:24]([CH3:23])=[C:25]([CH3:30])[N:26]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 3517702-Amino-5-methylthiazoleHCID 5049666Sodium triacetoxyborohydrideHCID 178520978HCID 178520978, compound

Product 1

HCID 178433160HCID 178433160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

800 mg (2.40 mmol) of trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Example 1 Step 3) and 274 mg (2.40 mmol) of 5-methylthiazol-2-amine are placed in a flask with 40 mL of DCM. 191 mg (3.60 mmol) of sodium triacetoxyborohydride is added and the RM is stirred at room temperature overnight 1N sodium hydroxide (2 mL) is added and the mixture is stirred at RT for 10 min. The RM is partitioned between DCM and water. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo. The product is purified by ISCO Combiflash Rf (80 g Si, iso-hexane→EtOAc, default setting). The product crystallized out on the column and had to be eluted with EtOAc (10% MeOH). The solvent is removed in vacuo and the product is crystallized from EtOAc, filtered and dried for 4 days under vacuum @50° C.

Workup

  1. additionis added
  2. customThe RM is partitioned between DCM and water
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe product is purified by ISCO Combiflash Rf (80 g Si, iso-hexane→EtOAc, default setting)
  8. customThe product crystallized out on the column
  9. washto be eluted with EtOAc (10% MeOH)
  10. customThe solvent is removed in vacuo
  11. customthe product is crystallized from EtOAc
  12. filtrationfiltered
  13. customdried for 4 days under vacuum @50° C.

Sources & evidence

ORD record
ord-5e89b6e3fef74904b281cb1a593568b0
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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