Triethylamine → HCID 57513822, compound

HRID 2368408Notes

Reaction equation

HRID 2368408 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.[NH2:49][C:50]1[S:51][C:52]([O:58][C:59]2[CH:66]=[CH:65][C:62]([C:63]#[N:64])=[CH:61][CH:60]=2)=[C:53]([CH:55]2[CH2:57][CH2:56]2)[N:54]=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]([C:13](=[O:15])[NH:49][C:50]1[S:51][C:52]([O:58][C:59]2[CH:66]=[CH:65][C:62]([C:63]#[N:64])=[CH:61][CH:60]=2)=[C:53]([CH:55]2[CH2:57][CH2:56]2)[N:54]=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 57476894HCID 57476894, compound

Product 1

HCID 57513822HCID 57513822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2-Benzyloxycarbonylamino-2-methyl-propionic acid (360 mg, 1.52 mmol), HBTU (576 mg, 1.52 mmol) and Et3N (0.21 mL, 1.5 mmol) in DMF (4 mL) was stirred at room temperature for 30 min. To this was added a solution of 4-(2-Amino-4-cyclopropyl-thiazol-5-yloxy)-benzonitrile (260 mg, 1.01 mmol) in DMF (4 mL). The mixture was heated at 85° C. for 18 h and partitioned between EtOAc and 3M HCl. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 477.1 (MH+).

Workup

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

Sources & evidence

ORD record
ord-5ef81903ed0041088b0281f6d3368a52
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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