4H,6H,7H-pyrano[3,4-d][1,2]oxazole-3-carboxylic acid → HCID 70656683, compound

HRID 872913Notes

Reaction equation

HRID 872913 reaction equation
[O:1]1[C:5]2[CH2:6][CH2:7][O:8][CH2:9][C:4]=2[C:3]([C:10]([OH:12])=O)=[N:2]1.[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[C:4]4[CH2:9][O:8][CH2:7][CH2:6][C:5]=4[O:1][N:2]=3)=[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 671704074H,6H,7H-pyrano[3,4-d][1,2]oxazole-3-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 70656683HCID 70656683, compoundYield 13.26%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 6,7-dihydro-4H-pyrano[3,4-d]isoxazole-3-carboxylic acid (0.174 g, 1.026 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.22 g, 0.789 mmol). The product was purified by LC/MS-trigger. Yield 13.26%. 1H-NMR (400 MHz; CDCl3): δ 1.23 (d, 3H), 2.93 (t, 2H), 3.91 (t, 2H), 4.27 (dd, 1H), 4.42 (dd, 1H), 4.50-4.60 (m, 1H), 4.89 (d, 2H), 6.63 (d, 1H), 7.37 (d, 1H), 7.50 (d, 1H), 7.59 (dd, 1H), 7.76-7.77 (m, 1H).

Workup

  1. customThe product was purified by LC/MS-trigger

Sources & evidence

ORD record
ord-add96ae39f3f457eb0ceb0a1b9d3bccc
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…