2-Amino-4-methylthiazole → HCID 50990952, compound

HRID 1908971Notes

Reaction equation

HRID 1908971 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH:2]=1.[CH3:17][C:18]1[N:19]=[C:20]([NH2:23])[S:21][CH:22]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:17][C:18]1[N:19]=[C:20]([NH:23][C:14](=[O:16])[C:10]2[CH:9]=[C:8]([O:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:13]=[CH:12][N:11]=2)[S:21][CH:22]=1

Participants

7

Reactant 4

HCID 741432-Amino-4-methylthiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 43144877HCID 43144877, compound

Product 1

HCID 50990952HCID 50990952, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 2 (3.0 g, 14 mmol, 1.0 eq), 4-methylthiazol-2-amine (1.66 g, 14.5 mmol, 1.05 eq), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (5.54 g, 14.5 mmol, 1.05 eq), and DIEA (2.6 mL, 15 mmol, 1.1 eq) were dissolved in DMF (69 mL) and stirred overnight at rt. The reaction was diluted with EtOAc and washed with H2O (2×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC afforded 1.5 g (35%) of the title compound as an off-white powder: 1H NMR (400 MHz, DMSO-d6) δ 8.65 (d, J=5.5 Hz, 1H), 8.59-8.57 (m, 2H), 7.79 (d, J=8.4 Hz, 1H), 7.60-7.56 (m, 2H), 7.31 (dd, J=5.5, 2.4 Hz, 1H), 6.89 (s, 1H), 2.29 (s, 3H); ES-MS [M+1]+: 313.1.

Workup

  1. washwashed with H2O (2×)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-2e641131eaa1422690c701706e67fb2a
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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