Dichloromethane → HCID 131729162, compound

HRID 907317Notes

Reaction equation

HRID 907317 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH:29]=O)[CH:7]=2)[CH2:3][CH2:2]1.[N:32]1(C(OC(C)(C)C)=O)[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:59]CCl>>[ClH:59].[ClH:59].[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH2:29][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Product 1

HCID 131729162HCID 131729162, compound

Procedure

To a solution of the product of Example 75 step i) (400 mg) in dichloromethane (20 mL) was added piperazine-1-carboxylic acid, tert-butyl ester (534 mg) and the mixture stirred at room temperature for 10 minutes before the addition of sodium triacetoxyborohydride (608 mg). After stirring at room temperature for a further 24 hours the reaction mixture was diluted with dichloromethane and washed with water. The organic phase was then evaporated to dryness and the residue treated with 4M HCl in 1,4-dioxane (10 mL) with methanol being added to aid dissolution. The reaction was stirred at room temperature for 1 hour and then concentrated to dryness. The residue was stirred in methanol and the resulting precipitate collected by filtration, washing with methanol to give the title compound as a solid (190 mg).

Workup

  1. washwashed with water
  2. customThe organic phase was then evaporated to dryness
  3. additionthe residue treated with 4M HCl in 1,4-dioxane (10 mL) with methanol being
  4. additionadded
  5. dissolutiondissolution
  6. stirringThe reaction was stirred at room temperature for 1 hour
  7. concentrationconcentrated to dryness
  8. stirringThe residue was stirred in methanol
  9. filtrationthe resulting precipitate collected by filtration
  10. washwashing with methanol

Sources & evidence

ORD record
ord-43033afe879d47b3bdb691d453bf7046
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

Loading…