2-Amino-4-methylthiazole → HCID 86762172, compound

HRID 1908974Notes

Reaction equation

HRID 1908974 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([OH:15])=O)[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.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:17][C:18]1[N:19]=[C:20]([NH:23][C:13](=[O:15])[C:12]2[CH:16]=[C:8]([O:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:9]=[N:10][CH: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 51038393HCID 51038393, compound

Product 1

HCID 86762172HCID 86762172, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 6 (30 mg, 0.14 mmol, 1.0 eq), 4-methylthiazol-2-amine (19 mg, 0.17 mmol, 1.2 eq), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (110 mg, 0.289 mmol, 2.10 eq), and N,N-Diisopropylethylamine (38 mg, 0.29 mmol, 2.1 eq) were dissolved in CH2Cl2 (1.5 mL) and DMF (0.30 mL) and stirred at rt for 72 h. The reaction was quenched with water, and the layers were separated via phase separation. The organic layer was dried on air concentrator and purified by reverse-phase preparatory HPLC to afford 17 mg (38%) of the title compound as a mono-TFA salt: 1H NMR (400 MHz, DMSO-d6) δ 9.01 (d, J=1.7 Hz, 1H), 8.69 (d, J=2.8 Hz, 1H), 8.56 (d, J=2.8 Hz, 1H), 8.49 (dd, J=4.7, 1.2 Hz, 1H), 8.04 (t, J=2.2 Hz, 1H), 7.68 (ddd, J=8.4, 2.8, 1.2 Hz, 1H), 7.54 (dd, J=8.4, 4.7 Hz, 1H), 7.23 (d, J=1.2 Hz, 1H), 2.36 (d, J=1.0, 3H); ES-MS [M+1]+:313.1.

Workup

  1. customThe reaction was quenched with water
  2. customthe layers were separated via phase separation
  3. customThe organic layer was dried on air concentrator
  4. custompurified by reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-1d325f97f28c4393af32525ebd2a425f
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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