2-Amino-4-methylthiazole → HCID 86654696, compound

HRID 2401506Notes

Reaction equation

HRID 2401506 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]([CH3:18])[C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:10]=1)[C:5]([OH:7])=O.[CH3:19][C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=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>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]([CH3:18])[C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:10]=1)[C:5]([NH:25][C:22]1[S:23][CH:24]=[C:20]([CH3:19])[N:21]=1)=[O:7]

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 58318871HCID 58318871, compound

Product 1

HCID 86654696HCID 86654696, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Compound 13 (0.727 g, 2.94 mmol, 1.00 eq), 4-methylthiazol-2-amine (369 mg, 3.23 mmol, 1.10 eq), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.23 g, 3.23 mmol, 1.10 eq), and DIEA (563 μL, 3.23 mmol, 1.10 eq) were dissolved in CH2Cl2 (15 mL) and DMF (3 mL) and stirred rt for 48 h. The reaction was diluted with CH2Cl2 and washed with water (1×). The organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 587 mg (58%) of the title compound as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.88 (s, 1H), 8.68 (s, 2H), 7.58 (m, 1H), 7.45 (m, 1H), 7.18 (m, 1H), 6.81 (s, 1H), 3.39 (s, 3H), 2.28 (s, 3H); [M+1]+: 344.1.

Workup

  1. washwashed with water (1×)
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-56e44779f91d402fb42761cb457aa0c6
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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