Dimethylformamide → HCID 71483884, compound

HRID 2409927Notes

Reaction equation

HRID 2409927 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH2:23])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C=O)C.C(N(C(C)C)CC)(C)C.Cl[C:39]1[O:40][C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=1>CO>[O:40]1[C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=[C:39]1[NH:23][C@@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22][C@H:17]1[NH:16][C@H:12]1[CH2:13][CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 71233239HCID 71233239, compound

Product 1

HCID 71483884HCID 71483884, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a 1 dram vial was added (1R,2R)—N1-(1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (25 mg, 0.079 mmol), DMF (1 mL), diisopropyl ethyl amine (0.069 mL, 0.393 mmol) and 2-chlorobenzo[d]oxazole (0.013 mL, 0.118 mmol). The vial was capped and the reaction was stirred at 65° C. for 1 hr. After this time, the reaction was diluted with MeOH and purified using RP prep-HPLC. Two diastereomers were separated. The desired isomer had the shorter retention time. The fractions with the desired material were concentrated to give the product (1R,2R)—N1-(benzo[d]oxazol-2-yl)-N2-((S)-1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (16 mg, 0.036 mmol, 45.4% yield) as yellow solid. Anal. Calcd. for C24H29N5O3 m/z 435.5, found: 436.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 8.06-7.92 (m, 2 H), 7.37 (d, J=7.70 Hz, 1 H), 7.25-7.15 (m, 2 H), 7.06 (t, J=7.70 Hz, 1H), 6.65 (d, J=9.35 Hz, 2 H), 5.33-5.15 (m, 1 H), 3.67 (d, J=9.08 Hz, 1 H), 3.59 (d, J=11.28 Hz, 1 H), 3.44 (br. s., 1 H), 3.16-3.03 (m, 1 H), 2.89 (br. s., 2 H), 2.63 (br. s., 1 H), 2.40 (br. s., 1 H), 2.16 (d, J=11.28 Hz, 1 H), 2.00-1.91 (m, 1 H), 1.82 (d, J=9.63 Hz, 4 H), 1.71-1.58 (m, 3 H), 1.44 (d, J=9.35 Hz, 2 H); 13C NMR (126 MHz, CDCl3) δ ppm 162.09, 162.07, 154.71, 148.33, 126.15, 124.01, 121.2, 116.46, 112.55, 108.84, 59.37, 57.80, 53.01, 51.03, 48.07, 32.22, 31.92, 29.73, 24.84, 24.60, 22.91.

Workup

  1. customThe vial was capped
  2. custompurified
  3. customTwo diastereomers were separated
  4. concentrationThe fractions with the desired material were concentrated

Sources & evidence

ORD record
ord-e0216f14c43240c8925be3103dfc2a59
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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