4H,6H,7H-pyrano[3,4-d][1,2]oxazole-3-carboxylic acid → HCID 70657187, compound

HRID 872901Notes

Reaction equation

HRID 872901 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]([CH3:30])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[CH:22]=2)=[N:17]1>>[Cl:29][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])[CH3:30])[N:17]=2)[CH:28]=[CH:27][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 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70657187HCID 70657187, compoundYield 9.5%

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 (0.101 g, 0.598 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.12 g, 0.460 mmol). The product was purified by reverse phase flash chromatography. Yield 9.50%. 1H-NMR (400 MHz; CDCl3): δ 1.25 (d, 3H), 2.93 (t, 2H), 3.90 (t, 2H), 4.26 (dd, 1H), 4.42 (dd, 1H), 4.50-4.62 (m, 1H), 4.86-4.90 (m, 2H), 6.64 (d, 1H), 7.50 (d, 1H), 7.64 (d, 1H), 7.71 (d, 1H), 7.87 (dd, 1H), 7.95 (d, 1H).

Workup

  1. customThe product was purified by reverse phase flash chromatography

Sources & evidence

ORD record
ord-6030978810464df390671a6dab4f71ae
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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