Dimethylformamide → HCID 66576763, compound

HRID 1409412Notes

Reaction equation

HRID 1409412 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[CH:11]=[CH:10][C:9]([C:12]([OH:14])=O)=[N:8]2)[CH:4]=[N:3]1.[NH2:15][C@@H:16]([CH3:32])[CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:31])[CH:24]=2)=[N:19]1.CN(C=O)C>C(Cl)Cl>[Cl:31][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][C@@H:16]([NH:15][C:12]([C:9]3[CH:10]=[CH:11][N:7]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)[N:8]=3)=[O:14])[CH3:32])[N:19]=2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 79779409HCID 79779409, compound

Product 1

HCID 66576763HCID 66576763, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 1′-methyl-1′H-[1,4′-bipyrazole]-3-carboxylic acid (0.921 mmol, 177 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.767 mmol, 200 mg) using DMF (2 ml) as the solvent. DCM was added and evaporated. The residue was purified by flash chromatography. The product was further purified by dissolving it in DCM and washing three times with 1 M NaHCO3 and evaporating the separated DCM phase. 220 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.14 (d, 3H), 3.89 (s, 3H), 4.27-4.42 (m, 2H), 4.42-4.53 (m, 1H), 6.76 (d, 1H), 6.95 (d, 1H), 7.83-7.87 (m, 3H), 7.94 (dd, 1H), 8.06 (d, 1H), 8.16 (d, 1H), 8.18 (s, 1H), 8.21 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. customevaporated
  3. customThe residue was purified by flash chromatography
  4. customThe product was further purified
  5. dissolutionby dissolving it in DCM
  6. washwashing three times with 1 M NaHCO3
  7. customevaporating the separated DCM phase

Sources & evidence

ORD record
ord-e4a1889e1ab54540a909da91a44d4a00
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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