Hydrochloric Acid → HCID 44555483, compound

HRID 1966880Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[N:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:17](Cl)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>N1C=CC=CC=1>[S:13]1[CH:14]=[N:15][N:16]=[C:12]1[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:17](=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 95 °C

Procedure

Compound 100 (50 mg, 0.20 mmol) was suspended in pyridine (0.3 mL). Decanoyl chloride (39.1 mg, 0.21 mmol) was added gradually over 15 min. The reaction mixture was heated to 95° C. and stirred at this temperature for 1 h, then poured into 10% aqueous HCl solution and extracted with EtOAc (3×0.5 mL). The combined organic extracts were washed with water (3×5 mL), brine (3×5 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent yielded the product (80 mg, 0.20 mmol, 95%). It was recrystallized from hexanes/ethyl acetate to yield an analytical sample, mp 151-152° C.; 1H NMR (250 MHz, CD3OD) δ 0.88 (3, t, J=7.5 Hz), 1.24-1.45 (12, m), 1.68 (2, t, J=7.5 Hz), 2.37 (2, t, J=7.5 Hz), 7.72 (2, d, J=8.5 Hz), 7.79 (2, d, J=8.5 Hz), 8.49 (1, S); 13C NMR (125 MHz, CD3OD) δ 14.4, 23.7, 26.7, 30.3, 30.4, 30.5, 30.6, 33.0, 38.1, 102.4, 128.3, 137.5, 144.0, 145.0, 170.0, 174.9; MS (ESI+) 411.1 (M+H)+; HRMS (IonSpec. HiRES ESL+) calcd. for C18H27N4O3S2 (M+H)+411.1525, obsd. 411.1524.

Workup

extractionextracted with EtOAc (3×0.5 mL)
washThe combined organic extracts were washed with water (3×5 mL), brine (3×5 mL)
dry with materialdried over anhydrous Na2SO4
customEvaporation of the solvent

Sources & evidence

ORD record: ord-645bc2d83c2b46139de295e45f680c1c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420678B2

Reaction notes

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