Triethylamine → HCID 59625986, compound

HRID 401708Notes

Reaction equation

HRID 401708 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[F:49][C:50]1[CH:55]=[CH:54][C:53]([N:56]2[C:60]3[CH:61]=[CH:62][C:63]([C:65](O)=[O:66])=[CH:64][C:59]=3[N:58]=[CH:57]2)=[CH:52][CH:51]=1>C(Cl)Cl.O>[F:49][C:50]1[CH:51]=[CH:52][C:53]([N:56]2[C:60]3[CH:61]=[CH:62][C:63]([C:65]([N:1]4[CH2:2][CH:3]([N:5]5[CH2:6][CH2:7][N:8]([C:11]([C:13]6[S:14][CH:15]=[CH:16][N:17]=6)=[O:12])[CH2:9][CH2:10]5)[CH2:4]4)=[O:66])=[CH:64][C:59]=3[N:58]=[CH:57]2)=[CH:54][CH:55]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 43566624HCID 43566624, compoundHCID 59625677(4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone

Product 1

HCID 59625986HCID 59625986, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5e (0.058 g, 0.178 mmol) and HATU (0.081 g, 0.214 mmol) in CH2Cl2 (3 mL) was added Et3N (0.099 mL, 0.713 mmol). The mixture was stirred at room temperature for 30 min, and then 60f (0.050 g, 0.196 mmol) was added. The reaction mixture was stirred at room temperature overnight. Water (6 mL) was added and the mixture was extracted with EtOAc. The organic layer was dried over MgSo4 and concentrated. The crude product Cpd 1167 was purified by preparative reverse phase chromatography. MS m/z (M+H+) 491.2.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was dried over MgSo4
  4. concentrationconcentrated
  5. customThe crude product Cpd 1167 was purified by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-617e85f06ebb485190704dfc1da27f24
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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