Dimethylformamide → HCID 86714629, compound

HRID 1409338Notes

Reaction equation

HRID 1409338 reaction equation
[OH:1][C:2]([C:5]1[NH:9][N:8]=[C:7]([C:10]([OH:12])=O)[CH:6]=1)([CH3:4])[CH3:3].[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.C1C=CC2N(O)N=NC=2C=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:7]3[CH:6]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[NH:9][N:8]=3)=[O:12])[CH3:31])[N:17]=2)[CH:28]=[C:27]([F:29])[C:24]=1[C:25]#[N:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 58810641HCID 58810641, compoundHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 86714629HCID 86714629, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) using 5-(2-hydroxypropan-2-yl)-1H-pyrazole-3-carboxylic acid (0.646 mmol, 110 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.539 mmol, 150 mg) and only a catalytic amount of HOBt (0.054 mmol, 7.28 mg). DMF was used as the solvent. Water was added to the reaction mixture and the mixture was extracted it three times with DCM. The combined organics were washed twice with water. The organic phase was evaporated and the residue was purified by flash chromatography and preparative HPLC, respectively. 45.4 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.13 (d, 3H), 1.43 (s, 6H), 4.17-4.55 (m, 3H), 5.27 (bs, 1H), 6.37 (bs, 1H), 6.99 (d, 1H), 7.82 (d, 1H), 7.86 (d, 1H), 7.97 (s, 1H), 8.08 (bs, 1H), 12.94 (bs, 1H).

Workup

  1. customThe title compound was prepared
  2. extractionthe mixture was extracted it three times with DCM
  3. washThe combined organics were washed twice with water
  4. customThe organic phase was evaporated
  5. customthe residue was purified by flash chromatography and preparative HPLC

Sources & evidence

ORD record
ord-b2e9b4bb30b7456a9c87fd11faec5206
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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