6,7-Dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylic acid → HCID 70656046, compound

HRID 872926Notes

Reaction equation

HRID 872926 reaction equation
[NH2:1][C@@H:2]([CH3:18])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=2)=[N:5]1.[N:19]1[N:27]2[C:22]([O:23][CH2:24][CH2:25][CH2:26]2)=[CH:21][C:20]=1[C:28](O)=[O:29]>>[Cl:17][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][C@@H:2]([NH:1][C:28]([C:20]3[CH:21]=[C:22]4[O:23][CH2:24][CH2:25][CH2:26][N:27]4[N:19]=3)=[O:29])[CH3:18])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 219413866,7-Dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656046HCID 70656046, compound

Procedure

The title compound was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (200 mg, 0.767 mmol) and 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylic acid (168 mg, 0.997 mmol). The product was purified with flash-chromatography. Yield 251 mg (80%). 1H-NMR (400 MHz; CDCl3): δ 1.21 (d, 3H), 2.27-2.32 (m, 2H), 4.14-4.20 (m, 2H), 4.26-4.43 (m, 4H), 4.51-4.60 (m, 1H), 6.01 (s, 1H), 6.62 (d, 1H), 7.49 (d, 1H), 7.51 (d, 1H), 7.66 (d, 1H), 7.81-7.84 (m, 1H), 8.03 (d, 1H).

Workup

  1. customThe product was purified with flash-chromatography

Sources & evidence

ORD record
ord-6c79c8ae838349ab8e4e5739854ed179
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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