Sodium Carbonate → HCID 10195095, compound

HRID 1992301Notes

Reaction equation

HRID 1992301 reaction equation
ClC1N=[C:4]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[CH:15]3)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2N=1.C([O-])([O-])=O.[Na+].[Na+].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.[CH2:44](O)[CH2:45][CH2:46]C.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:17]1[C:18]2[C:14](=[CH:13][C:12]([NH:11][C:4]3[C:5]4[S:10][CH:9]=[CH:8][C:6]=4[CH:46]=[C:45]([C:38]4[CH:39]=[CH:40][C:35]([CH2:34][NH:33][C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=5)=[CH:36][CH:37]=4)[CH:44]=3)=[CH:20][CH:19]=2)[CH:15]=[N:16]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 22475299HCID 22475299, compoundHCID 59130356HCID 59130356, compoundHCID 68491240HCID 68491240, compound

Product 1

HCID 10195095HCID 10195095, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a mixture of N-(2-chlorothieno[3,2-d]pyrimidin-4-yl)-N-(1H-indazol-5-yl)amine (50 mg, 0.16 mmol), Na2CO3(aq) (2 M, 1.0 mL) in butanol/toluene (1:1, 4 mL) a stream of argon was bubbled through for 15 min. To the mixture was added 4-[(2-pyridinylamino)methyl]phenylboronic acid (0.15 g, 0.66 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.08 mmol) in a single portion. The resulting reaction mixture was heated to reflux for 24 h. On cooling, the solution was concentrated, taken up in EtOAc and washed with water. The organic layers were dried over anhyd sodium sulfate and concentrated in vacuo. The crude product was purified by silica gel column chromatography (gradient from 20% to 80% EtOAc/hexane) to give the product (25 mg). HPLC/MS: (M+H)+ 450.1 m/z. Retention time (LC-MS)=min. 1H NMR (CD3OD): 8.31 (2H, d); 8.11 (1H, s); 8.05 (1H, s); 7.96(1H, d); 7.91 (1H, d); 7.71(1H, d); 7.58 (1H, d); 7.47(4H, m); 6.61(2H, m); 4.55 (2H, s).

Workup

  1. customwas bubbled through for 15 min
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureto reflux for 24 h
  5. temperatureOn cooling
  6. concentrationthe solution was concentrated
  7. washwashed with water
  8. dry with materialThe organic layers were dried over anhyd sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by silica gel column chromatography (gradient from 20% to 80% EtOAc/hexane)

Sources & evidence

ORD record
ord-ffee1696f5d7469f9673c936aa0ac852
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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