6,7-Dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylic acid → HCID 66575740, compound

HRID 872908Notes

Reaction equation

HRID 872908 reaction equation
[N:1]1[N:9]2[C:4]([O:5][CH2:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[C:10]([OH:12])=O.[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:2]3[CH:3]=[C:4]4[O:5][CH2:6][CH2:7][CH2:8][N:9]4[N:1]=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 219413866,7-Dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 66575740HCID 66575740, compoundYield 53.3%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-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 recrystallization from acetonitrile and by flash-chromatography, respectively. Yield 53.3%. 1H-NMR (400 MHz; CDCl3): δ 1.19 (d, 3H), 2.26-2.34 (m, 2H), 4.18-4.34 (m, 5H), 4.41 (dd, 1H), 4.52-4.62 (m, 1H), 6.01 (s, 1H), 6.62 (d, 1H), 7.50 (d, 1H), 7.66 (d, 1H), 7.70-7.75 (m, 21-1).

Workup

  1. customThe product was purified by recrystallization from acetonitrile and by flash-chromatography

Sources & evidence

ORD record
ord-036af043b9f6444baa75cd7c3f923977
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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