Triethylamine → HCID 54767997, compound

HRID 1503287Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].C([O:8][C:9](=O)[CH:10]([NH2:34])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[CH:13]=1)C.C([N:38](CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][S:2]([NH:34][CH:10]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)[CH:13]=1)[C:9]([NH2:38])=[O:8])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 30 °C

Procedure

2-Methane sulfonylamino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (39) was prepared as follows: MeSO2Cl (0.3 g, 2.6 mmol) was added to a solution of compound 33 (0.2 g, 0.5 mmol) prepared in Example 8 and triethylamine (0.5 mL) in CHCl3 (15 mL) at 0° C. The resulting mixture was shaken at 30° C. for 48 hours, and then washed with water (4 mL). The solvent was removed to give crude compound 38 (LC/MS: m/z=479.2 [M+H]+ (Calc: 478.2)), which was dissolved in NH3 (2 mL 28% aqueous and 4 mL 7N in MeOH), and heated to 120° C. for 2 hours under microwave. The reaction mixture was diluted with CHCl3 (45 mL), washed with water (10 mL), concentrated and purified by column (Silica gel, TCM/MeOH 10/1) to give compound 39 as a brown solid (60 mg, 30% in two steps): 1H-NMR (400 MHz, CDCl3) δ: 7.61-7.63 (m, 1H), 7.41-7.42 (m, 1H), 7.3-7.34 (m, 4H), 7.0-7.18 (m, 8H), 6.13 (br, 1H, NH), 5.57 (br, 1H, NH), 5.2 (d, 1H, 7.9 Hz), 4.19-4.25 (m, 1H), 3.32-3.37 (m, 1H), 3.19-3.25 (m, 1H), 2.54 (s, 3H); LC/MS: m/z=450.1 [M+H]+ (Calc: 449.5).

Workup

washwashed with water (4 mL)
customThe solvent was removed
customto give crude compound 38 (LC/MS: m/z=479.2 [M+H]+ (Calc: 478.2)), which

Sources & evidence

ORD record: ord-ee6b171463bb4c07a51f11c55c6a78ed
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212139B2

Reaction notes

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