Dimethylformamide → HCID 70981269, compound

HRID 1409333Notes

Reaction equation

HRID 1409333 reaction equation
[N:1]1[C:2]([C:10]([OH:12])=O)=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12.[NH2:13][C@@H:14]([CH3:31])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[C:27]([F:29])[C:24]([C:25]#[N:26])=[C:23]([Cl:30])[CH:22]=2)=[N:17]1.CN(C=O)C>O>[Cl:30][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:10]([C:2]3[N:1]=[C:5]4[CH2:6][CH2:7][CH2:8][CH2:9][N:4]4[CH:3]=3)=[O:12])[CH3:31])[N:17]=2)[CH:28]=[C:27]([F:29])[C:24]=1[C:25]#[N:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 445585605,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 70981269HCID 70981269, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid (2.58 mmol, 428 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (1.717 mmol, 479 mg). DMF (10 ml) was used as the solvent. The reaction mixture was diluted with water and extracted three times with DCM. The combined organics were washed twice with water. The organic phase was evaporated. The crude product was purified by flash chromatography. 515 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.07 (d, 3H), 1.78-1.94 (m, 4H), 2.76 (t, 2H), 3.95 (t, 2H), 4.24-4.31 (m, 1H), 4.33-4.46 (m, 2H), 7.01 (d, 1H), 7.43 (s, 1H), 7.84 (d, 1H), 7.90-7.95 (m, 1H), 8.00 (s, 1H), 8.08 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. extractionextracted three times with DCM
  3. washThe combined organics were washed twice with water
  4. customThe organic phase was evaporated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d6a94e287680414e822e152cfe36a29e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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