HCID 57437983, compound → HCID 86659256, compound

HRID 1803846Notes

Reaction equation

HRID 1803846 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[C:10]([N:17]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH:9]=2)[CH2:4][CH2:3]1.[CH2:30]([O:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][N:42]=[C:41]2[NH2:47])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>N1C=CC=CC=1>[CH2:30]([O:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][N:42]=[C:41]2[NH:47][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:9][C:10]=1[N:17]([CH:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)[C:18](=[O:23])[C:19]([F:20])([F:22])[F:21])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 57437983HCID 57437983, compoundHCID 86659257HCID 86659257, compound

Product 1

HCID 86659256HCID 86659256, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

4-(4-Methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzoyl chloride (10.04 mmol), in dry pyridine (100 mL), under a nitrogen atmosphere, cooled to 4° C., was treated with 5-benzyloxy-1H-indazol-3-ylamine (2 g, 8.37 mmol) in pyridine (35 mL) and stirred for 3 hours. The mixture was concentrated in vacuo. The residue was added to iced water (350 mL) and extracted with EtOAc (400 mL and 2×200 mL). The combined organic layers were dried over anhydrous sodium sulfate. After removal of the volatiles a brown solid was obtained that was taken in Et20 (200 mL), stirred 2 hours at room temperature, filtered and dried at 50° C. under vacuum to afford 4 g of title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue was added to iced water (350 mL)
  3. extractionextracted with EtOAc (400 mL and 2×200 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. customAfter removal of the volatiles a brown solid
  6. customwas obtained
  7. stirringstirred 2 hours at room temperature
  8. filtrationfiltered
  9. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-b75eb6b429e842bab6e06b054e514c3a
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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