5-[(Morpholin-4-yl)methyl]-1,2-oxazole-3-carboxylic acid--hydrogen chloride (1/1) → HCID 70656581, compound

HRID 872727Notes

Reaction equation

HRID 872727 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.Cl.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[O:31][N:30]=[C:29]([C:32](O)=[O:33])[CH:28]=2)[CH2:22][CH2:21]1>>[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:32]([C:29]3[CH:28]=[C:27]([CH2:26][N:23]4[CH2:22][CH2:21][O:20][CH2:25][CH2:24]4)[O:31][N:30]=3)=[O:33])[CH3:18])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 173895725-[(Morpholin-4-yl)methyl]-1,2-oxazole-3-carboxylic acid--hydrogen chloride (1/1)HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656581HCID 70656581, compoundYield 16.9%

Procedure

(S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(morpholinomethyl)isoxazole-3-carboxamide was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (200 mg, 0.690 mmol) and 5-(morpholinomethyl)isoxazole-3-carboxylic acid hydrochloride (206 mg, 0.828 mmol). The product was purified by reverse phase Flash-chromatography. Yield 16.9%. 1H-NMR (400 MHz; MeOD): δ 1.26 (d, 3H), 2.47-2.56 (m, 4H), 3.65-3.71 (m, 4H), 3.75 (d, 2H), 4.28-4.44 (m, 2H), 4.53-4.63 (m, 1H), 6.59 (t, 1H), 6.77 (d, 1H), 7.71 (d, 1H), 7.78 (dd, 1H), 7.88 (dd, 1H), 8.08 (dd, 1H).

Workup

  1. customThe product was purified by reverse phase Flash-chromatography

Sources & evidence

ORD record
ord-a876a64994924fb59c69b5a66dad5753
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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