1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86703775, compound

HRID 1849897Notes

Reaction equation

HRID 1849897 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([O:18][C:19]2[C:27]([CH:28]3[CH2:30][CH2:29]3)=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([F:31])[CH:20]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH3:43][S:44]([NH2:47])(=[O:46])=[O:45]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][C:19]2[C:27]([CH:28]3[CH2:30][CH2:29]3)=[CH:26][C:22]([C:23]([NH:47][S:44]([CH3:43])(=[O:46])=[O:45])=[O:24])=[C:21]([F:31])[CH:20]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 86703774HCID 86703774, compound

Product 1

HCID 86703775HCID 86703775, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-(1-benzhydrylazetidin-3-yloxy)-5-cyclopropyl-2-fluorobenzoic acid (100 mg, 0.24 mmol), EDCI (69 mg, 0.36 mmol), DMAP (44 mg, 0.36 mmol) and methanesulfonamide (34 mg, 0.36 mmol) in DCM (15 mL) was stirred at room temperature for 18 h. The mixture was diluted with DCM (10 mL) and washed with HCl (2 N, 15 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Combiflash (20%-50% CH3CN/H2O in 0.1% NH4HCO3) to give target compound (40 mg, 34%) as a pale yellow solid. LCMS (ESI) Method A: RT=5.29 min, m/z: 495.1 [M+H]+. 1H-NMR (500 MHz, MeOH-d4,): δ 7.54-7.46 (m, 10H), 7.29 (d, J=8.0 Hz, 1H), 6.64 (d, J=12.0 Hz, 1H), 5.83 (s, 1H), 5.29-5.26 (m, 1H), 4.75-4.71 (m, 2H), 4.41-4.38 (m, 2H), 3.37 (s, 3H), 2.22-2.18 (m, 1H), 1.03-0.99 (m, 2H), 0.75-0.42 (m, 2H).

Workup

  1. washwashed with HCl (2 N, 15 mL×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Combiflash (20%-50% CH3CN/H2O in 0.1% NH4HCO3)

Sources & evidence

ORD record
ord-bdbb07f8279c480fa37575d2a8f4fc51
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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