2-Aminothiazole → HCID 86659561, compound

HRID 1431021Notes

Reaction equation

HRID 1431021 reaction equation
C([C:4]1[C:12]([S:13][C:14]2[N:15]([CH3:19])[CH:16]=[CH:17][N:18]=2)=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6](C(C)C)[C:5]=1[O:23][C:24]1[CH:29]=[CH:28][C:27]([P:30]([O:36][CH:37]([CH3:39])[CH3:38])([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])=[CH:26][CH:25]=1)(C)C.[NH2:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC(N(C)C)=O>C(Cl)Cl.CN(C=O)C>[CH:33]([O:32][P:30]([C:27]1[CH:28]=[CH:29][C:24]([O:23][C:5]2[CH:6]=[C:7]([C:8](=[O:10])[NH:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)[CH:11]=[C:12]([S:13][C:14]3[N:15]([CH3:19])[CH:16]=[CH:17][N:18]=3)[CH:4]=2)=[CH:25][CH:26]=1)(=[O:31])[O:36][CH:37]([CH3:39])[CH3:38])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 31374DimethylacetamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86659563HCID 86659563, compound

Product 1

HCID 86659561HCID 86659561, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of diisopropyl 3-[4-(diisopropoxy-phosphoryl)-phenoxy]-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzoic acid (68 mg, 0.139 mmol), 2-aminothiazole (28 mg, 0.277 mmol), HATU (66 mg, 0.174 mmol), DMA (0.058 mL, 0.35 mmol) and 0.7 mL of DMF were stirred for 16 h at rt, diluted with CH2Cl2, washed with water, brine, dried and evaporated. The residue was adsorbed to SiO2 and subjected to MPLC on a 12 g column of SiO2 eluting with % MeOH in CH2Cl2 (time): 1% (5 min), 2.5% (10 min), 5% (10 min) which provided 50 mg (63%) of the title compound: 1H NMR (500 MHz, DMSO-d6): δ 1.20 (d, 6H, J=6 Hz). 1.28 (d, 6H, J=6 Hz), 3.66 (s, 3H). 4.56 (m, 2H), 6.95 (t, 1H, J=2 Hz), 7.13 (d, 1H, J=1 Hz), 7.15 (dd, 2H, J=8, 3 Hz), 7.30 (br s, 1H), 7.50 (d, 1H, J=1 Hz), 7.55 (d, 1H, J=3 Hz). 7.60 (br s, 1H), 7.67 (br s, 1H), 7.73 (dd, 2H, J=12, 8 Hz); LCMS (m/z): 573.7 [C26H29N4O5PS2+H]+.

Workup

  1. washwashed with water, brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-1b8b932a24e045218774f57df00fe058
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

Loading…