Toluene → HCID 131733362, compound

HRID 518931Notes

Reaction equation

HRID 518931 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:23]3[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)=[C:17]([C:24](O)=[O:25])[CH:16]=2)=[C:11]([C:27]([N:29]2[C@H:38]([CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]2)=[O:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C.C1(C)C=CC=CC=1.[Si:61]([O:68][C:69]1[CH:74]=[CH:73][C:72]([NH:75][C:76]2[CH:77]=[C:78]3[CH:84]=[CH:83][N:82]([CH3:85])[C:79]3=[N:80][CH:81]=2)=[CH:71][CH:70]=1)([C:64]([CH3:67])([CH3:66])[CH3:65])([CH3:63])[CH3:62]>ClCCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:23]3[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)=[C:17]([C:24]([N:75]([C:72]3[CH:71]=[CH:70][C:69]([O:68][Si:61]([C:64]([CH3:67])([CH3:65])[CH3:66])([CH3:63])[CH3:62])=[CH:74][CH:73]=3)[C:76]3[CH:77]=[C:78]4[CH:84]=[CH:83][N:82]([CH3:85])[C:79]4=[N:80][CH:81]=3)=[O:25])[CH:16]=2)=[C:11]([C:27]([N:29]2[C@H:38]([CH2:39][N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]2)=[O:28])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 117831217HCID 117831217, compoundHCID 131733363HCID 131733363, compound

Product 1

HCID 131733362HCID 131733362, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The acid obtained in Step B (9 g, 11.8 mmol) is dissolved in 90 mL of 1,2-dichloroethane. 1.9 mL of 1-chloro-N,N,2-trimethylpropenylamine (14 mmol) are added thereto. After stirring for 3 hours at ambient temperature, 90 mL of toluene and 4.62 g of N-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-1-methyl-1H-pyrrolo[2,3-b]pyridin-5-amine (Preparation 3″, 13 mmol) are added. The reaction mixture is heated at 110° C. for 20 hours. After returning to ambient temperature, the reaction mixture is washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue obtained is purified by chromatography over silica gel (dichloromethane/ethanol gradient) to yield the expected product.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated at 110° C. for 20 hours
  3. customAfter returning to ambient temperature
  4. washthe reaction mixture is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue obtained
  9. customis purified by chromatography over silica gel (dichloromethane/ethanol gradient)

Sources & evidence

ORD record
ord-aee84fecb90844aab953f240504a0b60
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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