4-Methylmorpholine → HCID 86752866, compound

HRID 965142Notes

Reaction equation

HRID 965142 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[CH2:10][CH:11](N1C=C(C2C=CC(C3C=CC=CC=3)=CC=2)N=C1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H:34]1[CH2:51][C:50]2=[CH:52][N:43]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=32)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][NH:36][C:35]1=[O:53].CC[N:56]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:32])[CH:10]([CH:34]1[CH2:51][C:50]2=[CH:52][N:43]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=32)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][NH:36][C:35]1=[O:53])[CH2:11][C:12]([NH2:56])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18341435HCID 18341435, compoundHCID 67729859HCID 67729859, compound

Product 1

HCID 86752866HCID 86752866, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 2-(4-biphenyl-4-yl-imidazol-1-yl)succinic acid 4-benzyl ester (450 mg, 1.05 mmol), (10S)-10-amino-9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraene (284 mg, 0.95 mmol), EDCI (302 mg, 1.5 mmol), HOBT (142 mg, 1.05 mmol), N-methylmorpholine (0.14 mL) and DMAP (50 mg) in DMF (10 mL) was stirred at room temperature overnight. The solution was diluted with 100 mL of EtOAc and washed with brine and saturated NaHCO3 and dried. The crude product obtained after removal of solvents was purified by column chromagraphy to give (3RS,10S)-3-(4-biphenyl-4-yl-imidazol-1-yl)-N-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl-succinamic acid benzyl ester.

Workup

  1. washwashed with brine and saturated NaHCO3
  2. customdried
  3. customThe crude product obtained
  4. customafter removal of solvents
  5. customwas purified by column chromagraphy

Sources & evidence

ORD record
ord-ab2c2050500148d3a9e95aafdb0ab789
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

Loading…