1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67173637, compound

HRID 872819Notes

Reaction equation

HRID 872819 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[NH:6][N:5]=1)(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.[NH2:43][CH2:44][CH2:45][C:46]1[O:50][N:49]=[C:48]([C:51]2[CH:58]=[CH:57][C:54]([C:55]#[N:56])=[C:53]([Cl:59])[C:52]=2[CH3:60])[CH:47]=1>C(Cl)Cl>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:43][CH2:44][CH2:45][C:46]2[O:50][N:49]=[C:48]([C:51]3[CH:58]=[CH:57][C:54]([C:55]#[N:56])=[C:53]([Cl:59])[C:52]=3[CH3:60])[CH:47]=2)=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 67168593HCID 67168593, compound

Product 1

HCID 67173637HCID 67173637, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Acetyl-1H-pyrazole-5-carboxylic acid (31 mg; 0.203 mmol) and DIPEA (0.106 ml) were dissolved in 5 ml of dry DCM. HOBt hydrate (47 mg; 0.304 mmol) and EDCI (58 mg; 0.304 mmol) were added at RT. 4-(5-(2-aminoethyl) isoxazol-3-yl)-2-chloro-3-methylbenzonitrile (53 mg; 0.203 mmol) was added and the reaction was stirred at RT for 4 h. DCM 10 ml of was added and organic layer washed with 1M HCl, saturated NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was triturated with n-heptane to give the title product 32 mg. 1H-NMR (400 MHz; d6-DMSO): δ 2.44 (s, 3H), 2.51 (s, 3H), 3.12 (t, 2H), 3.63 (m, 2H), 6.75 (s, 1H), 7.30 (bs, 1H), 7.62 (d, 1H), 7.94 (d, 1H), 8.73 (bs, 1H), 14.20 (s, 1H).

Workup

  1. washorganic layer washed with 1M HCl, saturated NaHCO3 and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was triturated with n-heptane

Sources & evidence

ORD record
ord-8f3d5251b442460786647dcb5dc35efe
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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