1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(Benzo[d]thiazol-2-yl)-N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)acetamide

HRID 1591739Notes

Reaction equation

HRID 1591739 reaction equation
[CH:1]([N:4]([CH3:22])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[C@H:7]([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:6]1)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[S:44]1[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:46]=[C:45]1[CH2:53][C:54]([O-])=[O:55].[Na+]>C1COCC1.C(Cl)Cl>[S:44]1[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:46]=[C:45]1[CH2:53][C:54]([NH:11][C@H:8]1[CH2:9][CH2:10][C@@H:5]([N:4]([CH:1]([CH3:3])[CH3:2])[CH3:22])[CH2:6][C@H:7]1[CH2:12][S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:14])=[O:15])=[O:55]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 47002634Sodium 2-(1,3-benzothiazol-2-yl)acetateHCID 68468828(1R*,3R*,4S*)-N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)cyclohexane-1,4-diamine

Product 1

HCID 111679482-(Benzo[d]thiazol-2-yl)-N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)acetamideYield 60.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1R,3R,4S)—N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)-cyclohexane-1,4-diamine (see 30b) (70 mg, 0.216 mmol), EDCI (50 mg, 0.260 mmol), HOBT (35 mg, 0.260 mmol), and sodium 2-(benzo[d]thiazol-2-yl)acetate (56 mg, 0.260 mmol) in THF (5 mL) was stirred overnight at room temperature. The mixture was dilute with CH2Cl2 (25 mL) and washed with water, brine and evaporated. The residue was chromatographed on silica gel (6% NH4OH/MeOH/CH2Cl2) to give the product (65 mg). MS found: (M+1)+: 500.49.

Workup

  1. washwashed with water, brine
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (6% NH4OH/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-29bde9a0a6ac4bccad881bc204be7fef
Source dataset
uspto-grants-2007_11
Patent number
US07291615B2

Reaction notes

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