Nitrogen → HCID 67128462, compound

HRID 1189441Notes

Reaction equation

HRID 1189441 reaction equation
N#N.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][C:13]([CH3:15])=[N:12][C:11]=2[C:16]([OH:18])=O)[CH:7]=[CH:8][CH:9]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.Cl.[NH2:51][C:52]1[N:53]=[C:54]([CH2:57][C:58]2[S:62][C:61]([C:63](=[O:65])[CH3:64])=[CH:60][CH:59]=2)[S:55][CH:56]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:63]([C:61]1[S:62][C:58]([CH2:57][C:54]2[S:55][CH:56]=[C:52]([NH:51][C:16]([C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=3)=[O:18])[N:53]=2)=[CH:59][CH:60]=1)(=[O:65])[CH3:64]

Participants

9

Reactant 6

HCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 534307265-(3-Chloro-phenyl)-2-methyl-oxazole-4-carboxylic acidHCID 67128443HCID 67128443, compound

Product 1

HCID 67128462HCID 67128462, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(3-chloro-phenyl)-2-methyl-oxazole-4-carboxylic acid (57 mg, 0.24 mmol) in CH2Cl2 (2.4 mL) was treated sequentially with DMAP (7 mg, 0.06 mmol), HOBt (39 mg, 0.29 mmol), EDC.HCl (114 mg, 0.60 mmol) and DIPEA (0.16 mL, 0.96 mmol) and the resulting mixture was stirred at rt for 30 min. This solution was then treated with 1-[5-(4-amino-thiazol-2-ylmethyl)-thiophen-2-yl]-ethanone hydrochloride (66 mg, 0.24 mmol) and the reaction mixture was stirred for 2 days at rt. CH2Cl2 (20 mL) was then added and the org. phase was washed with water (15 mL) followed by 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 (6:4 hept:EA) gave the title compound as a yellow oil. TLC: rf (6:4 hept-EA)=0.19. LC-MS-conditions 02: tR=1.18 min, [M+H]+=458.08.

Workup

  1. stirringthe reaction mixture was stirred for 2 days at rt
  2. washphase was washed with water (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 (6:4 hept:EA)

Sources & evidence

ORD record
ord-e56eef1e76144a7b8625eb16d2b7a5fa
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

Loading…