Nitrogen → HCID 67128468, compound

HRID 1189440Notes

Reaction equation

HRID 1189440 reaction equation
N#N.[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([OH:16])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.Cl.[NH2:49][C:50]1[N:51]=[C:52]([CH2:55][C:56]2[S:60][C:59]([C:61](=[O:63])[CH3:62])=[CH:58][CH:57]=2)[S:53][CH:54]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:61]([C:59]1[S:60][C:56]([CH2:55][C:52]2[S:53][CH:54]=[C:50]([NH:49][C:14]([C:10]3[N:11]=[CH:12][O:13][C:9]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:16])[N:51]=2)=[CH:57][CH:58]=1)(=[O:63])[CH3:62]

Participants

9

Reactant 6

HCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 67128443HCID 67128443, compound

Product 1

HCID 67128468HCID 67128468, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-phenyl-1,3-oxazole-4-carboxylic acid (40 mg, 0.21 mmol) in CH2Cl2 (2.0 mL) was treated sequentially with DMAP (6 mg, 0.05 mmol), HOBt (34 mg, 0.25 mmol), EDC.HCl (101 mg, 0.53 mmol) and DIPEA (0.14 mL, 0.85 mmol) and the resulting mixture was stirred at rt for 15 min. This solution was then added to a solution of 1-[5-(4-amino-thiazol-2-ylmethyl)-thiophen-2-yl]-ethanone hydrochloride (58 mg, 0.21 mmol) in dry CH2Cl2 (0.5 mL) and the reaction mixture was stirred for 2 days at rt. CH2Cl2 (20 mL) was then added and the org. phase was washed with brine (15 mL). The org. phase was then dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept:EA) followed by HPLC gave the title compound as a yellow solid. LC-MS-conditions 05: tR=0.98 min, [M+H]+=410.16.

Workup

  1. stirringthe reaction mixture was stirred for 2 days at rt
  2. washphase was washed with brine (15 mL)
  3. dry with materialphase was then dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (1:1 hept:EA)

Sources & evidence

ORD record
ord-43ab375bcc454f23868bff639a6bd332
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

Loading…