(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 136377296, compound

HRID 1409330Notes

Reaction equation

HRID 1409330 reaction equation
[NH:1]1[C:5]2[NH:6][C:7]([C:9]([OH:11])=O)=[CH:8][C:4]=2[CH:3]=[N:2]1.[NH2:12][C@@H:13]([CH3:30])[CH2:14][N:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:27]=[C:26]([F:28])[C:23]([C:24]#[N:25])=[C:22]([Cl:29])[CH:21]=2)=[N:16]1>>[Cl:29][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][N:15]([CH2:14][C@@H:13]([NH:12][C:9]([C:7]3[NH:6][C:5]4[NH:1][N:2]=[CH:3][C:4]=4[CH:8]=3)=[O:11])[CH3:30])[N:16]=2)[CH:27]=[C:26]([F:28])[C:23]=1[C:24]#[N:25]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 136350684HCID 136350684, compound

Product 1

HCID 136377296HCID 136377296, compoundYield 18.5%

Procedure

The title compound was prepared using the procedure described in Example 3(h), starting from 1,6-dihydropyrrolo[2,3-c]pyrazole-5-carboxylic acid (0.280 mmol, 0.042 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.215 mmol, 0.080 g). The crude product was purified by preparative HPLC. 0.0164 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 1.29 (d, 3H), 4.27-4.34 (m, 1H), 4.36-4.43 (m, 1H), 4.50-4.60 (m, 1H), 6.75-6.79 (m, 2H), 7.58 (s, 1H), 7.60-7.65 (m, 1H), 7.69 (d, 1H), 7.79-7.82 (m, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f1a6fc631f8347b390adbbaa3d2e07fb
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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