1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66576440, compound

HRID 1409303Notes

Reaction equation

HRID 1409303 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:54][C@@H:55]([CH3:73])[CH2:56][N:57]1[CH:61]=[CH:60][C:59]([C:62]2[CH:69]=[C:68]([F:70])[C:65]([C:66]#[N:67])=[C:64]([Cl:71])[C:63]=2[F:72])=[N:58]1>CN(C=O)C.O.CCOC(C)=O>[Cl:71][C:64]1[C:63]([F:72])=[C:62]([C:59]2[CH:60]=[CH:61][N:57]([CH2:56][C@@H:55]([NH:54][C:7]([C:5]3[NH:6][C:2]([CH3:1])=[N:3][CH:4]=3)=[O:9])[CH3:73])[N:58]=2)[CH:69]=[C:68]([F:70])[C:65]=1[C:66]#[N:67]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86714622HCID 86714622, compoundHCID 178433052HCID 178433052, compound

Product 1

HCID 66576440HCID 66576440, compoundYield 59.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-1H-imidazole-4-carboxylic acid (0.202 mmol, 0.026 g) was dissolved in DMF (5 ml) under nitrogen atmosphere. EDCI (0.202 mmol, 0.039 g), DIPEA (0.270 mmol, 0.035 g) and HBTU (0.034 mmol, 0.013 g) were added and the resulting mixture was stirred for 20 min at RT. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-3,6-difluorobenzonitrile (0.135 mmol, 0.04 g) dissolved in DMF (2 ml) was added and the resulting mixture was stirred at RT for 3 days. The mixture was diluted with water and EtOAc, washed with 2M Na2CO3, water and brine. The combined organics were dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.0324 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4) δ ppm 1.23 (d, 3H), 2.38 (s, 3H), 4.28-4.47 (m, 2H), 4.48-4.58 (m, 1H), 6.77-6.82 (m, 1H), 7.46 (s, 1H), 7.77 (d, 1H), 7.83-7.96 (m, 1H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at RT for 3 days
  3. washwashed with 2M Na2CO3, water and brine
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-efe837c3c34843ae879e278030298b1f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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