Ethanol → tert-Butyl (1-{5-chloro-3-[1-hydroxy-2-(isopropylamino)ethyl]-2-methoxy-4-methylphenyl}ethyl)carbamate

HRID 511013Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[C:12]([CH:18]2[CH2:20][O:19]2)[C:11]=1[O:21][CH3:22])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(O)C.[CH3:27][CH:28]([NH2:30])[CH3:29].CCN(C(C)C)C(C)C>>[Cl:16][C:14]1[C:13]([CH3:17])=[C:12]([CH:18]([OH:19])[CH2:20][NH:30][CH:28]([CH3:29])[CH3:27])[C:11]([O:21][CH3:22])=[C:10]([CH:8]([NH:7][C:6](=[O:23])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:9])[CH:15]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 6363Isopropylamine

HCID 81531Diisopropylethylamine

HCID 123871195tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-oxiran-2-ylphenyl)ethyl]carbamate

Product 1

HCID 86666930tert-Butyl (1-{5-chloro-3-[1-hydroxy-2-(isopropylamino)ethyl]-2-methoxy-4-methylphenyl}ethyl)carbamateYield 5%

Conditions

Temperature: 80 °C

Procedure

tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-oxiran-2-ylphenyl)ethyl]carbamate (100 mg, 0.29 mmol, from Example 190, Step 1) was stirred in ethanol (2.0 mL, 34 mmol), 2-propanamine (120 μL, 1.5 mmol) and DIPEA (260 μL, 1.5 mmol) was added. The mixture was stirred at 80° C. over the weekend. Purification by preparative LC/MS (pH 10) gave the desired compound (5.7 mg, 5%). LCMS calculated for C20H34ClN2O4 (M+H)+: m/z=401.2. found: 401.1.

Workup

customPurification by preparative LC/MS (pH 10)

Sources & evidence

ORD record: ord-04d68ed5ee9d4313b8f2f782c7cf8833
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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