Dicyclohexylcarbodiimide → HCID 58658622, compound

HRID 720940Notes

Reaction equation

HRID 720940 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:13]3[C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=3[CH2:11][CH2:10][C@H:9]([NH:24][C:25](=[O:27])[CH3:26])[C:8]=2[CH:28]=1)(O)=[O:2].C1CCC(N=C=NC2CCCCC2)CC1.[NH2:44][CH2:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>CN(C1C=CN=CC=1)C.ClCCl>[C:25]([NH:24][C@@H:9]1[C:8]2[CH:28]=[C:4]([C:1]([NH:44][CH2:45][CH2:46][CH2:47][N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)=[O:2])[CH:5]=[CH:6][C:7]=2[C:13]2[C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=2[CH2:11][CH2:10]1)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 61055N-(3-Aminopropyl)morpholineHCID 16114799HCID 16114799, compound

Product 1

HCID 58658622HCID 58658622, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-[(5S)-3-carboxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (0.3 g; 0.779 mmol), (Med. Chem. Res. 1991, 142), DCCI (0.322 g; 1.55 mmol), DMAP (0.069 g; 0.389 mmol) and 4-(3-aminopropyl)morpholine (170 μl; 1.17 mmol) in dichloromethane (6 ml) was stirred under argon atmosphere overnight. After removal of the insoluble material by filtration, the residue was purified on reverse phase silica eluting with a gradient of 40–50% methanol/ammonium carbonate buffer (2 g/l, pH7). The appropriate fractions were evaporated to dryness and triturated in ether to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-N-(3-morpholinopropyl)-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-carboxamide as a white solid.

Workup

  1. customAfter removal of the insoluble material
  2. filtrationby filtration
  3. customthe residue was purified on reverse phase silica eluting with a gradient of 40–50% methanol/ammonium carbonate buffer (2 g/l, pH7)
  4. customThe appropriate fractions were evaporated to dryness
  5. customtriturated in ether

Sources & evidence

ORD record
ord-b07e5472041d4bcca3410b70fc11f08c
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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