1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68454447, compound

HRID 2085706Notes

Reaction equation

HRID 2085706 reaction equation
[CH3:1][N:2]([CH3:50])[C:3](=[O:49])[CH2:4][C@@H:5]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41](O)=[O:42])=[CH:35][C:34]=3[O:44][CH3:45])=[CH:29][CH:28]=2)=[O:26])(=[O:23])=[O:22])=[CH:17][C:16]=1[N+:46]([O-:48])=[O:47])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:51]([NH2:56])[C:52]([CH3:55])([CH3:54])[CH3:53].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C(=O)C.ClC(Cl)C>[CH3:45][O:44][C:34]1[CH:35]=[C:36]([CH2:39][CH2:40][C:41]([NH:56][CH2:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:42])[CH:37]=[CH:38][C:33]=1[C:30]1[CH:29]=[CH:28][C:27]([C:25]([NH:24][S:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C@@H:5]([CH2:6][S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:4][C:3]([N:2]([CH3:50])[CH3:1])=[O:49])=[C:16]([N+:46]([O-:48])=[O:47])[CH:17]=2)(=[O:23])=[O:22])=[O:26])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 79882NeopentylamineHCID 68455470HCID 68455470, compound

Product 1

HCID 68454447HCID 68454447, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of Example 126C (50 mg, 0.069 mmol), neopentylamine (21 mg, 0.20 mmol), EDCI (20 mg, 0.104 mmol), and HOBT (15 mg, 0.104 mmol) in N,N-dimethylacetamide (1 mL) and dichloroethane (0.5 mL) at room temperature was stirred for 16 hours. The mixture was concentrated, dissolved in 1:1 DMSO/methanol (1.0 mL) and purified by reverse phase preparative HPLC (using a C-18 column and a solvent system increasing in gradient from 20 to 95% acetonitrile/water containing 0.1% TFA) to provide the desired product. MS (ESI(−)) m/e 788 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ8.89 (br d, 1H), 8.57 (d, 1H), 7.90 (d, 2H), 7.85 (dd, 1H), 7.70(br t, 1H), 7.58 (d, 2H), 7.30-7.12 (m, 7H), 7.00 (d, 1H), 6.90 (dd, 1H), 4.45 (m, 1H), 3.75 (s, 3H), 3.42 (t, 2H), 2.90 (s, 3H), 2.79 (s, 3H), 3.00-2.70 (m, 8H), 0.80 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in 1:1 DMSO/methanol (1.0 mL)
  3. custompurified by reverse phase preparative HPLC (
  4. temperaturea solvent system increasing in gradient from 20 to 95% acetonitrile/water containing 0.1% TFA)

Sources & evidence

ORD record
ord-986b0c0d0223468484e13dcb4f55657d
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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