1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66576438, compound

HRID 1409313Notes

Reaction equation

HRID 1409313 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:8]=1)#[N:2].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[NH2:45][C@@H:46]([CH3:63])[CH2:47][N:48]1[CH:52]=[CH:51][C:50]([C:53]2[CH:60]=[C:59]([F:61])[C:56]([C:57]#[N:58])=[C:55]([Cl:62])[CH:54]=2)=[N:49]1>C(Cl)Cl.CN(C=O)C>[Cl:62][C:55]1[CH:54]=[C:53]([C:50]2[CH:51]=[CH:52][N:48]([CH2:47][C@@H:46]([NH:45][C:12]([C:10]3[N:11]=[C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]4[CH:9]=3)=[O:14])[CH3:63])[N:49]=2)[CH:60]=[C:59]([F:61])[C:56]=1[C:57]#[N:58]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 231554816-Cyanoimidazo[1,2-a]pyridine-2-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 66576438HCID 66576438, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

6-Cyanoimidazo[1,2-a]pyridine-2-carboxylic acid (0.770 mmol, 0.144 g), HOBt (0.770 mmol, 0.104 g) and DIPEA (1.539 mmol, 0.199 g) were dissolved in DCM (5 ml) and DMF (1 ml). EDCI (0.770 mmol, 0.148 g) was added and the resulting mixture was stirred for 10 min at RT. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.592 mmol, 0.22 g) dissolved in small amount of DCM was added and the reaction mixture was stirred overnight at RT. The mixture was diluted with DCM, washed with 1M Na2CO3 and water. The organic phase was dried, filtered and evaporated. The crude product was purified by trituration from ACN. 0.054 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.15 (d, 3H), 4.31-4.45 (m, 2H), 4.46-4.57 (m, 1H), 7.00 (d, 1H), 7.61-7.66 (m, 1H), 7.72-7.77 (m, 1H), 7.86-7.92 (m, 2H), 7.93-7.96 (m, 1H), 8.35-8.37 (m, 1H), 8.69 (d, 1H), 9.34-9.37 (m, 1H).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred overnight at RT
  3. washwashed with 1M Na2CO3 and water
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by trituration from ACN

Sources & evidence

ORD record
ord-bafe63ed9dc344fc8c96f4b07ff50371
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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