1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86714650, compound

HRID 1409389Notes

Reaction equation

HRID 1409389 reaction equation
[CH:1]1([N:4]2[CH:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[N:5]2)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:42][C@@H:43]([CH3:60])[CH2:44][N:45]1[CH:49]=[CH:48][C:47]([C:50]2[CH:57]=[C:56]([F:58])[C:53]([C:54]#[N:55])=[C:52]([Cl:59])[CH:51]=2)=[N:46]1>C(Cl)Cl>[Cl:59][C:52]1[CH:51]=[C:50]([C:47]2[CH:48]=[CH:49][N:45]([CH2:44][C@@H:43]([NH:42][C:9]([C:6]3[CH:7]=[CH:8][N:4]([CH:1]4[CH2:2][CH2:3]4)[N:5]=3)=[O:11])[CH3:60])[N:46]=2)[CH:57]=[C:56]([F:58])[C:53]=1[C:54]#[N:55]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 670305061-cyclopropyl-1H-pyrazole-3-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 86714650HCID 86714650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Cyclopropyl-1H-pyrazole-3-carboxylic acid (0.30 g, 1.29 mmol) was dissolved in DCM (20 ml). EDCI (0.692 g, 3.61 mmol), HOBt (0.487 g, 3.61 mmol) and DIPEA (0.932 g, 7.22 mmol) were added at 0° C. to the solution. The resulting mixture was stirred at 0° C. for 15 min. (S)-4-(1-(2-Aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.502 g, 1.8 mmol) dissolved in DCM (2 ml) was added and the mixture was stirred overnight. The reaction mixture was quenched by the addition of water and extracted with DCM. The organic layer was evaporated and the residue was purified by flash chromatography. Yield: 400 mg. 1H-NMR (400 MHz; DMSO-d6): δ 0.97-1.17 (m, 7H), 3.74-3.80 (m, 1H), 4.26-4.41 (m, 3H), 6.53 (d, 1H), 7.01 (d, 1H), 7.82-7.87 (m, 3H), 7.96 (s, 1H), 8.14 (d, 1H).

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionextracted with DCM
  4. customThe organic layer was evaporated
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-256545c8138f434eb738909f510b40cd
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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