1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66914349, compound

HRID 2104805Notes

Reaction equation

HRID 2104805 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([NH:24][CH2:25][C:26]3[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=3)[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:35]([F:38])([F:37])[F:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][O:40][C:41](=[O:44])[CH2:42][NH2:43].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.C(#N)C.O>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([NH:43][CH2:42][C:41]([O:40][CH3:39])=[O:44])=[O:31])=[CH:33][CH:34]=3)[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:35]([F:38])([F:36])[F:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69221Glycine methyl esterHCID 757711-HydroxybenzotriazoleHCID 66913537HCID 66913537, compound

Product 1

HCID 66914349HCID 66914349, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-{[3-(3-benzyl-8-trifluoromethyl-quinolin-4-yl)-phenylamino]-methyl}-benzoic acid (130 mg, 0.254 nmol), glycine methyl ester (35 mg, 0.279 mmol) morpholine (102 mg, 1.014 mmol), EDCI (58 mg, 0.304 mmol), and HOBT (41 mg, 0.304 mmol) in CH2Cl2 (15 ml) were combined at room temperature under a nitrogen atmosphere. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 15 hrs. Quenching with brine (15 ml), separation, drying MgSO4 of the organics and concentration in vacuo. RP-HPLC (gradient water:acetonitrile) afforded the ester as an off white powder (88 mg, 61% Yield). MS (ESI) m/z 582.

Workup

  1. customwere combined at room temperature under a nitrogen atmosphere
  2. customQuenching with brine (15 ml), separation
  3. dry with materialdrying MgSO4 of the organics and
  4. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-8d3642b09fb74df3bff12e951def80b5
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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