Dimethylamine → HCID 22638775, compound

HRID 2416246Notes

Reaction equation

O=[CH:2][CH2:3][CH:4]1[CH2:6][CH:5]1[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[N:9]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:8]=1.C[NH:29][CH3:30].C(O[BH-](O[C:41](=O)[CH3:42])OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:47]1COCC1>C(O)C.O>[CH2:30]([N:29]([CH2:41][CH3:42])[CH2:2][CH2:3][CH:4]1[CH2:6][CH:5]1[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[N:9]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:8]=1)[CH3:47]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-[2-(2-oxo-ethyl)-cyclopropyl]-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (50 mg, 0.13 mmol), dimethylamine (0.2 ml of a 2M solution in THF, 0.4 mmol), and 112 mg (0.53 mmol) sodium triacetoxyborohydride in ethyl alcohol (2 ml), was stirred for 12 hr at 70° C. Sodium hydroxide (15 equivalents of a 1N solution) was added and the mixture was stirred for 45 min at 75° C. The reaction mixture was cooled, diluted with water (3 ml), and extracted twice with ethyl acetate (10 ml). The ethyl acetate extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC to give 3-[2-(2-diethylaminoethyl)-cyclopropyl]-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (8.2 mg, 22%). MS m/e 282.22 (MH+).

Workup

stirringthe mixture was stirred for 45 min at 75° C
temperatureThe reaction mixture was cooled
extractionextracted twice with ethyl acetate (10 ml)
dry with materialThe ethyl acetate extracts were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-5a8977c6b2f944a689e4a0e5e5ffd2ed
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06822100B2

Reaction notes

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