1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67171695, compound

HRID 872543Notes

Reaction equation

HRID 872543 reaction equation
[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([C:10]([OH:12])=O)[CH:6]=1)([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:43][C@@H:44]([CH3:60])[CH2:45][N:46]1[CH:50]=[CH:49][C:48]([C:51]2[CH:58]=[CH:57][C:54]([C:55]#[N:56])=[C:53]([Cl:59])[CH:52]=2)=[N:47]1>C(Cl)Cl.CN(C=O)C>[Cl:59][C:53]1[CH:52]=[C:51]([C:48]2[CH:49]=[CH:50][N:46]([CH2:45][C@@H:44]([NH:43][C:10]([C:7]3[CH:6]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[O:9][N:8]=3)=[O:12])[CH3:60])[N:47]=2)[CH:58]=[CH:57][C:54]=1[C:55]#[N:56]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-Hydroxybenzotriazole2×HCID 81531Diisopropylethylamine2×HCID 67168640860371-76-22×HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 67171695HCID 67171695, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

5-(2-hydroxypropan-2-yl)isoxazole-3-carboxylic acid (0.088 g, 0.515 mmol) and DIPEA (0.090 ml, 0.515 mmol) were dissolved in 5 ml of dry DCM. Anhydrous HOBt (0.070 g, 0.515 mmol), and EDCI (0.099 g, 0.515 mmol) were added. After stirring at RT for 30 min the (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.112 g, 0.430 mmol) dissolved in 1 ml of dry DMF was added to the reaction mixture. After overnight stirring at RT a mixture of 5-(2-hydroxypropan-2-yl)isoxazole-3-carboxylic acid (0.088 g, 0.515 mmol), DIPEA (0.090 ml, 0.515 mmol), anhydrous HOBt (0.070 g, 0.515 mmol) and EDCI (0.099 g, 0.515 mmol) dissolved in 5 ml of dry DCM was added to the reaction mixture. After 3 h the solvents were evaporated and the residue was purified by CombiFlash using MeOH in DCM as an eluent. Product fractions were combined and evaporated to give 58 mg of the product. 1H-NMR (400 MHz; CDCl3): δ 1.23 (d, 3H), 1.65 (s, 6H), 4.26 (m, 1H), 4.43 (m, 1H), 4.58 (m, 1H), 6.60 (s, 1H), 6.63 (d, 1H), 7.49 (d, 1H), 7.68 (d, 1H), 7.83 (d, 1H), 7.90 (d, 1H), 8.07 (d, 1H).

Workup

  1. additionwas added to the reaction mixture
  2. additionwas added to the reaction mixture
  3. customAfter 3 h the solvents were evaporated
  4. customthe residue was purified by CombiFlash
  5. customevaporated

Sources & evidence

ORD record
ord-bd73625fe6174250b93b146f77c6e2fe
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…