Triethylamine → HCID 67019922, compound

HRID 1673228Notes

Reaction equation

HRID 1673228 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[O:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]([NH2:18])[C:11]3=[CH:10][C:9]=2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:4]([Cl:28])[CH:3]=1.CCN(CC)CC.[Br:36][CH2:37][CH2:38][CH2:39][C:40](Cl)=[O:41].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:36][CH2:37][CH2:38][CH2:39][C:40]([NH:18][CH:17]1[C:11]2[C:12](=[N:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[Cl:28])=[C:9]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[CH:10]=2)[O:14][C:15]([CH3:20])([CH3:19])[CH2:16]1)=[O:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 702254-Bromobutyryl chlorideHCID 516892Sodium BicarbonateHCID 67019926HCID 67019926, compound

Product 1

HCID 67019922HCID 67019922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-(4-bromo-2-chlorophenyl)-6-(4-chloro-phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-amine (303 mg, 0.63 mmol) and NEt3 (221 μL, 1.6 mmol) in 10 mL of CH2Cl2 was added 4-bromobutyryl chloride (110 μL, 0.95 mmol). After stirring at rt for 16 h, the reaction mixture was combined with saturated aq NaHCO3 (20 mL). The aq layer was separated and extracted with CH2Cl2 (3×20 mL). The organic layers were combined, dried over MgSO4, and concentrated to afford the product.

Workup

  1. customThe aq layer was separated
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto afford the product

Sources & evidence

ORD record
ord-df6b828828d64b7d91024143d3924a64
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

Loading…