HCID 67305053, compound → HCID 136367448, compound

HRID 1922001Notes

Reaction equation

HRID 1922001 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:37]3[CH:42]=[CH:41][N:40]=[C:39]([NH:43][CH3:44])[N:38]=3)[CH:9]=[C:10]2[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH:24]3[C:36]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:30]4[C:25]3=[CH:26][CH:27]=[CH:28][CH:29]=4)=[O:21])[CH2:16][CH2:15]2)=[CH:5][CH:4]=1>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:37]3[CH:42]=[CH:41][N:40]=[C:39]([NH:43][CH3:44])[N:38]=3)[CH:9]=[C:10]2[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH:24]3[C:36]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:30]4[C:25]3=[CH:26][CH:27]=[CH:28][CH:29]=4)=[O:21])[CH2:16][CH2:15]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 67305053HCID 67305053, compound

Product 1

HCID 136367448HCID 136367448, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottom flask equipped with rubber septum containing solution of (9H-fluoren-9-yl)methyl 4-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)piperidine-1-carboxylate 205 (0.41 g, 0.69 mmol) in chloroform (10 mL) was cooled to 0° C. Trifluoroborane dimethylsulfide complex (0.73 mL, 27.7 mmol) was added dropwise via syringe. The reaction mixture was stirred at 0° C. for 5 minutes and allowed to warm to room temperature overnight. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was extracted with saturated aqueous sodium bicarbonate (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated (rotary) to afford a brown solid (0.34 g). The crude compound was purified by column chromatography (silica gel) using 3.5% methanol/chloroform as the eluent and triturated with diethyl ether to afford 9H-fluoren-9-ylmethyl 4-({7-hydroxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)piperidine-1-carboxylate 206 as an orange-yellow solid (0.28 g). LC/MS (m/z): 573 [M+H].

Workup

  1. customA round-bottom flask equipped with rubber septum
  2. additionTrifluoroborane dimethylsulfide complex (0.73 mL, 27.7 mmol) was added dropwise via syringe
  3. temperatureto warm to room temperature overnight
  4. customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (200 mL)
  5. extractionThe organic layer was extracted with saturated aqueous sodium bicarbonate (100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated (rotary)

Sources & evidence

ORD record
ord-5345512bf23e40a28ad0c7de6ce72d43
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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