4-Chlorobenzoic Acid → HCID 59813447, compound

HRID 1925375Notes

Reaction equation

HRID 1925375 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14]4)=[C:4]2[CH:3]=[N:2]1.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:21][C:17]2[C:18]3[C:13](=[CH:12][C:11]([O:10][C:9]4[CH:8]=[CH:7][N:6]=[C:5]5[NH:1][N:2]=[CH:3][C:4]=45)=[CH:20][CH:19]=3)[CH:14]=[CH:15][CH:16]=2)=[O:28])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic Acid2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 67520710HCID 67520710, compound

Product 1

HCID 59813447HCID 59813447, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(1H-Pyrazolo[3,4-b]pyridin-4-yloxy)naphthalen-1-amine (25 mg, 0.09 mmol), 4-chlorobenzoic acid (16 mg, 0.10 mmol) and TBTU (35 mg, 0.108 mmol) were dissolved in DMF (0.75 mL). Hunig's base (18 mg, 0.14 mmol) was then added and the reaction mixture was stirred at RT for 16 h. Additional 4-chlorobenzoic acid (6 mg, 0.036 mmol) and TBTU (12 mg, 0.036 mmol) were added to the reaction and stirring was continued for 3 days. The reaction mixture was concentrated in vacuo. The remaining dark brown residue was purified by silica gel chromatography (0% to 2% MeOH in DCM) to yield 4-chloro-N-(6-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)-1-naphthalenyl)benzamide as an off-white solid. MS (ESI, pos. ion) m/z: 415.0 (M+1). MS (ESI pos. ion) m/z: 415.0 (M+H). Calc'd for C23H15ClN4O2−414.85.

Workup

  1. stirringstirring
  2. waitwas continued for 3 days
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe remaining dark brown residue was purified by silica gel chromatography (0% to 2% MeOH in DCM)

Sources & evidence

ORD record
ord-2bb35063ecc34dbe9d71fc6002363a04
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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