1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59570826, compound

HRID 2071174Notes

Reaction equation

HRID 2071174 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C@H:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)[S:5][CH:6]=1.[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:22]=1)[C:17](O)=[O:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:18][CH2:17][C:16]1[CH:20]=[C:21]([CH:22]=[C:14]([C:13]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:7]2[C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)=[O:12])[CH:15]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 42078478HCID 42078478, compoundHCID 57496016HCID 57496016, compound

Product 1

HCID 59570826HCID 59570826, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-4-methyl-2-(pyrrolidin-2-yl)thiazole (511 mg, 3.037 mmol) and 3-(hydroxymethyl)-5-(methoxycarbonyl)benzoic acid (702.5 mg, 3.34 mmol) in DCM (50 mL) were added diisopropylthylamine (3 mL, excess), HOBt (410 mg, 3.34 mmol) and EDCI (754.1 mg, 3.948 mmol). The resulting solution was stirred at room temperature for overnight. The reaction mixture was diluted with chloroform, washed with sodium bicarbonate saturated aqueous solution and separated. The aqueous layer was extracted one more time with chloroform. The combined organic layers were concentrated to give a residue, which was purified with flash chromatography to produce the desired compound (840 mg). 1H NMR (300 MHz, CDCl3), d: 8.011 (m, 1.5H), 7.876 (br, 0.5H), 7.683 (m, 1H), 6.749 (m, 1H), 5.579 (m, 0.7H), 5.061 (br, 0.3H), 4.641 (br, 1.2H), 4.525 (br, 0.8H), 3.875 (m, 3H), 3.692 (m, 1H), 3.457 (m, 1H), 2.345 (m, 5H), 2.034 (m, 2H).

Workup

  1. washwashed with sodium bicarbonate saturated aqueous solution
  2. customseparated
  3. extractionThe aqueous layer was extracted one more time with chloroform
  4. concentrationThe combined organic layers were concentrated
  5. customto give a residue, which
  6. customwas purified with flash chromatography

Sources & evidence

ORD record
ord-4783a73db163483bb6a923d1f50afa21
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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