(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 178461761, compound

HRID 872907Notes

Reaction equation

HRID 872907 reaction equation
[N:1]1[NH:2][C:3]([C:10]([OH:12])=O)=[C:4]2[C:9]=1[CH2:8][CH2:7][CH2:6][CH2:5]2.[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>>[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:3]3[NH:2][N:1]=[C:9]4[C:4]=3[CH2:5][CH2:6][CH2:7][CH2:8]4)=[O:12])[CH3:31])[N:17]=2)[CH:28]=[C:27]([F:29])[C:24]=1[C:25]#[N:26]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 178524920HCID 178524920, compound

Product 1

HCID 178461761HCID 178461761, compoundYield 65.9%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 4,5,6,7-tetrahydro-2H-indazole-3-carboxylic acid (0.078 g, 0.466 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.1 g, 0.359 mmol). The product was purified by flash chromatography. Yield 65.9%. 1H-NMR (400 MHz; DMSO-d6): δ 1.11 (d, 3H), 1.55-1.71 (m, 4H), 2.53-2.60 (m, 4H), 4.27 (dd, 1H), 4.35 (dd, 1H), 4.38-3.46 (m, 1H), 7.00 (d, 1H), 7.83-7.87 (m, 2H), 7.90-7.97 (m, 2H), 12.66 (s, 1H).

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-b19fdae02c204cbd84c3e25aaf2f621d
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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