Triethylamine → HCID 21073226, compound

HRID 1373629Notes

Reaction equation

HRID 1373629 reaction equation
[CH3:1][C:2]1[C:3]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([CH3:19])[C:4]=2[N:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=O)[N:7]=1.FC(F)(F)C(O)=O.[F:27][C:28]1[CH:37]=[C:36]2[C:31]([CH:32]=[CH:33][CH:34]=[C:35]2[N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:30][CH:29]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:27][C:28]1[CH:37]=[C:36]2[C:31]([CH:32]=[CH:33][CH:34]=[C:35]2[N:38]2[CH2:43][CH2:42][N:41]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:6]3[N:7]=[C:2]([CH3:1])[C:3]4[CH:17]=[CH:16][C:15](=[O:18])[N:14]([CH3:19])[C:4]=4[N:5]=3)[CH2:40][CH2:39]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 21073342HCID 21073342, compoundHCID 69372946HCID 69372946, compound

Product 1

HCID 21073226HCID 21073226, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4,8-dimethyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yloxy)-butyraldehyde (78.4 mg, 0.30 mmol) and 1-(7-fluoro-naphthalen-1-yl)-piperazine trifluoroacetic acid (105 mg, 0.306 mmol) were combined in methylene chloride and triethylamine (63 mg, 0.63 mmol) was added. The mixture was stirred in a vial over sieves for 10 min. Sodium triacetoxyborohydride (89 mg, 0.420 mmol) was added and the reaction was stirred overnight. The reaction was quenched slowly with water and the mixture was filtered. The residue was partitioned between CH2Cl2 and water. The organic layer was washed with water and concentrated. Purification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of a 10% MeOH in CH2Cl2 solution) gave the title compound as a white foam (89 mg, 0.187 mmol, 62.4%). MS: APCI: M+1: 476.2 (Exact Mass: 475.24).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched slowly with water
  3. filtrationthe mixture was filtered
  4. customThe residue was partitioned between CH2Cl2 and water
  5. washThe organic layer was washed with water
  6. concentrationconcentrated
  7. customPurification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of a 10% MeOH in CH2Cl2 solution)

Sources & evidence

ORD record
ord-76da166903a0447b809879af4e6b5c4d
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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