2-Aminothiazole → HCID 57722952, compound

HRID 222294Notes

Reaction equation

HRID 222294 reaction equation
[CH3:1][N:2]([CH3:26])[S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:23]=[CH:22][C:14]3=[N:15][CH:16]=[C:17]([C:19]([OH:21])=O)[CH:18]=[C:13]3[C:12](=[O:24])[C:11]=2[CH:25]=1)(=[O:5])=[O:4].[NH2:27][C:28]1[S:29][CH:30]=[CH:31][N:32]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C=O)C.C(OC(=O)C)C>[CH3:1][N:2]([CH3:26])[S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:23]=[CH:22][C:14]3=[N:15][CH:16]=[C:17]([C:19]([NH:27][C:28]4[S:29][CH:30]=[CH:31][N:32]=4)=[O:21])[CH:18]=[C:13]3[C:12](=[O:24])[C:11]=2[CH:25]=1)(=[O:4])=[O:5]

Participants

8

Reactant 4

HCID 21552-AminothiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67411706HCID 67411706, compound

Product 1

HCID 57722952HCID 57722952, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude 7-{[(dimethylamino)sulfonyl]amino}-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-3-carboxylic acid (21 mg, 0.056 mmol), 2-aminothiazole (8 mg, 0.084 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (16 mg, 0.084 mmol), 1-hydroxybenzotriazole hydrate (11 mg, 0.084 mmol) and 4-dimethylaminopyridine (spatula tip) were dissolved in 2 mL of DMF and stirred for 18 h. The mixture was diluted in ethylacetate and the organic layer was washed with saturated aqueous sodium bicarbonate and brine, then dried over sodium sulfate and concentrated. The residue was purified via reverse phase HPLC (20-100% acetonitrile/water gradient, 0.05% trifluoroacetic acid modifier) to afford the title compound. 1H NMR (600 MHz, DMSO-d6) δ 13.06 (br s, 1H); 10.59 (br s, 1H); 9.47 (d, 1H); 9.13 (d, 1H); 8.02 (d, 1H); 7.81 (d, 1H); 7.61 (dd, 1H); 7.57 (d, 1H); 7.50 (d, 1H); 7.27-7.33 (m, 2H); 2.74 (s, 6H); LRMS (APCI) calc'd for (C20H17N5O4S2) [M+H]+, 456.1; found 456.1.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified via reverse phase HPLC (20-100% acetonitrile/water gradient, 0.05% trifluoroacetic acid modifier)

Sources & evidence

ORD record
ord-fcc3a1103abe4e14a3da06d9a68f5bfe
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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