1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70656555, compound

HRID 872693Notes

Reaction equation

HRID 872693 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[N:29]=[C:28]([C:30]([OH:32])=O)[O:27][N:26]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH: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.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[NH2:63][C@@H:64]([CH3:81])[CH2:65][N:66]1[CH:70]=[CH:69][C:68]([C:71]2[CH:78]=[C:77]([F:79])[C:74]([C:75]#[N:76])=[C:73]([Cl:80])[CH:72]=2)=[N:67]1>ClCCl>[Cl:80][C:73]1[CH:72]=[C:71]([C:68]2[CH:69]=[CH:70][N:66]([CH2:65][C@@H:64]([NH:63][C:30]([C:28]3[O:27][N:26]=[C:25]([C:23]4[N:22]=[CH:21][N:20]([C:1]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[CH:24]=4)[N:29]=3)=[O:32])[CH3:81])[N:67]=2)[CH:78]=[C:77]([F:79])[C:74]=1[C:75]#[N:76]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 671735983-(1-trityl-1H-imidazol-4-yl)-1,2,4-oxadiazole-5-carboxylic acid

Product 1

HCID 70656555HCID 70656555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Into a flask containing 3-(1-trityl-1H-imidazol-4-yl)-1,2,4-oxadiazole-5-carboxylic acid (0.148 g, 0.350 mmol) and anhydrous HOBt (0.047 g; 0.350 mmol), dichloromethane (2 ml), DIPEA (0.122 ml; 0.700 mmol) and EDCI (0.067 g; 0.350 mmol) were added and stirred for 10 min at RT. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.100 g, 0.269 mmol) dissolved in 2 ml of dichloromethane was added and the resulting mixture stirred overnight. Next day the temperature was raised to 50° C. and more EDCI (0.067 g; 0.350 mmol) was added. The reaction mixture was allowed to react with stirring for 4 h. DCM was added and the organic layer was extracted with 1M Na2CO3 and water. The organic layer was then evaporated and the residue purified with flash chromatography. LC-MS: [M+1]=684.133.

Workup

  1. additionwere added
  2. additionwas added
  3. stirringthe resulting mixture stirred overnight
  4. temperatureNext day the temperature was raised to 50° C.
  5. customto react
  6. stirringwith stirring for 4 h
  7. extractionthe organic layer was extracted with 1M Na2CO3 and water
  8. customThe organic layer was then evaporated
  9. customthe residue purified with flash chromatography

Sources & evidence

ORD record
ord-dc8a223b149449ec93bd79af2de318a5
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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