1-Propanol → (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

HRID 872613Notes

Reaction equation

HRID 872613 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:15])[C:3]=1[C:4]#[N:5].[CH2:16](O)[CH2:17][CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/[N:45]=N/C(OC(C)C)=O)=O)C>>[NH2:45][C@@H:17]([CH3:18])[CH2:16][N:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:7]=[C:6]([F:15])[C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[N:14]1

Participants

5

Reactant 4

HCID 10311-PropanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 671697812-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile

Product 1

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Procedure

2-Chloro-6-fluoro-4-(1H-pyrazol-5-yl)benzonitrile (0.74 g, 3.3 mmol) was reacted with (S)-(−)-2-tert-butoxycarbonylamino)-1-propanol (0.88 g, 5.0 mmol) in the presence of triphenylphosphine and DIAD using the method of Example 99. After Boc-deprotection 0.45 g (49%) of the title compound was obtained. 1H-NMR (400 MHz; d6-DMSO): δ 0.95 (d, 3H), 3.17-3.28 (m, 1H), 4.01 (dd, 2H), 7.03 (d, 1H), 7.85-7.91 (m, 2H), 7.99 (m, 1H).

Sources & evidence

ORD record
ord-b56bfc21fcd44c4d8514f334cf8baed8
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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