Isoxazole-5-carbonyl chloride → HCID 86594935, compound

HRID 1825852Notes

Reaction equation

HRID 1825852 reaction equation
[NH2:1][CH:2]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:3]([N:5]1[CH2:8][CH:7]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6]1)=[O:4].[O:24]1[C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=[N:25]1>>[NH2:1][CH:2]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[C:3]([N:5]1[CH2:8][CH:7]([N:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:29]([C:28]2[O:24][N:25]=[CH:26][CH:27]=2)=[O:30])[CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 2736707Isoxazole-5-carbonyl chlorideHCID 22139658HCID 22139658, compound

Product 1

HCID 86594935HCID 86594935, compound

Procedure

{1-[2-Amino-3-(4-chloro-phenyl)-propionyl]-azetidin-3-yl}-cyclohexylamine was acylated with isoxazole-5-carbonyl chloride in a manner similar to that described for 6 above and then the Boc protecting group removed by treatment with a solution of HCl in dioxane and MeOH to furnish isoxazole-5-carboxylic acid {1-[2-amino-3-(4-chloro-phenyl)-propionyl]-azetidin-3-yl}-cyclohexyl-amide. 1H NMR (400 MHz, CDCl3) δ 8.33–8.29 (m, 1H), 7.32–7.12 (m, 4H), 6.77–6.71 (m, 1H), 4.54 (br, 2H), 4.34–3.80 (m, 2H), 3.60–3.40 (m, 2H), 3.20–2.70 (m, 2H), 2.60–2.05 (m, 2H), 1.86–1.60 (m, 4H), 1.60–1.00 (m, 4H), 0.90–0.78 (m, 3H); MS Calcd for C22H27ClN4O3 [M+H], 431. Found, 431.

Workup

  1. customthe Boc protecting group removed by treatment with a solution of HCl in dioxane and MeOH

Sources & evidence

ORD record
ord-157748a760634a45a69c4db5404d6f0f
Source dataset
uspto-grants-2006_05
Patent number
US07049323B2

Reaction notes

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