Triethylamine → HCID 57513819, compound

HRID 2368405Notes

Reaction equation

HRID 2368405 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[F:49][C:50]1[CH:69]=[CH:68][C:53]([O:54][C:55]2[S:59][C:58]([NH2:60])=[N:57][C:56]=2[C:61]2[CH:66]=[CH:65][C:64]([F:67])=[CH:63][CH:62]=2)=[CH:52][CH:51]=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]([C:13](=[O:15])[NH:60][C:58]1[S:59][C:55]([O:54][C:53]2[CH:68]=[CH:69][C:50]([F:49])=[CH:51][CH:52]=2)=[C:56]([C:61]2[CH:66]=[CH:65][C:64]([F:67])=[CH:63][CH:62]=2)[N:57]=1)([CH3:17])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57476893HCID 57476893, compound

Product 1

HCID 57513819HCID 57513819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2-benzyloxycarbonylamino-2-methyl-propionic acid (10.5 g, 44.2 mmol), HBTU (16.8 g, 44.3 mmol) and Et3N (6.2 mL, 45 mmol) in DMF (50 mL) was stirred at room temperature for 2 h. To this was added a solution of 5-(4-Fluoro-phenoxy)-4-(4-fluoro-phenyl)-thiazol-2-ylamine (9.62 g, ca. 32 mmol with some impurities present) in DMF (50 mL). The mixture was heated at 85° C. for 18 h and partitioned between EtOAc and, sequentially, 3M HCl and aqueous KOH. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 524.2 (MH+).

Workup

  1. temperatureThe mixture was heated at 85° C. for 18 h
  2. custompartitioned between EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-ed7291ab136049068a97f996b13ac7ca
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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