4-Tert-Butylaniline → HCID 59813799, compound

HRID 1925340Notes

Reaction equation

HRID 1925340 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21](Cl)=[O:22])=[CH:16][CH:15]=[CH:14]3)=[N:3][CH:2]=1.[C:24]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C>C1COCC1>[CH3:27][C:24]([C:28]1[CH:29]=[CH:30][C:31]([NH:32][C:21]([C:17]2[C:18]3[C:13](=[CH:12][C:11]([O:10][C:4]4[C:5]5[CH:9]=[CH:8][NH:7][C:6]=5[N:1]=[CH:2][N:3]=4)=[CH:20][CH:19]=3)[CH:14]=[CH:15][CH:16]=2)=[O:22])=[CH:33][CH:34]=1)([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 86608622HCID 86608622, compound

Product 1

HCID 59813799HCID 59813799, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

THF (1.3 mL) was added to 6-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-1-naphthoyl chloride (84.0 mg, 0.259 mmol) in a 10 mL round bottom flask, followed by 4-t-butyl aniline (62.4 μL, 0.389 mmol) and Hunig's base (45.1 μL, 0.259 mmol). The resulting solution was stirred for 14 h and then transferred to a 50 mL flask. To this solution was added ˜5 g of silica gel. The resulting slurry was concentrated by reduced pressure. The impregnated silica gel was loaded into a dry pack column cartridge and the crude mixture was purified through Biotage chromatography (Hex:EtOAc). The collected product was repurified through trituration with DCM. MS (ESI, pos. ion) m/z: 437.1 (M+1). Mass Calc'd for C18H15NO3: 436.51.

Workup

  1. customtransferred to a 50 mL flask
  2. additionTo this solution was added ˜5 g of silica gel
  3. concentrationThe resulting slurry was concentrated by reduced pressure
  4. customthe crude mixture was purified through Biotage chromatography (Hex:EtOAc)
  5. customThe collected product was repurified through trituration with DCM

Sources & evidence

ORD record
ord-a77d47a8d8764003b31d19febbc01e58
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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