HCID 58967444, compound → HCID 57461497, compound

HRID 1663203Notes

Reaction equation

HRID 1663203 reaction equation
[NH2:1][C:2]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH:7]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:8](=[O:15])[NH:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1)=[O:5].[CH:29](OCC)(OCC)OCC.CCN(CC)CC>>[CH:17]1([CH2:16][CH:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[C:26]([O:27][CH3:28])[CH:25]=[CH:24][CH:23]=3)[N:1]=[CH:29]2)[C:8]([NH:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[O:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 58967444HCID 58967444, compoundHCID 131729228HCID 131729228, compound

Product 1

HCID 57461497HCID 57461497, compound

Conditions

Temperature
130 °C

Procedure

2-amino-N-(3-cyclohexyl-1-oxo-1-(thiazol-2-ylamino)propan-2-yl)-3-methoxybenzamide (0.5 g, 1.24 mmol) was dissolved in (EtO)3CH:Et3N (4:1, 2 mL) and the reaction was heated to 130° C. overnight. All solvents were removed. The crude product was purified via preparative HPLC. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95-1.31 (m, 6H) 1.54-1.77 (m, 4H) 1.85 (s, 1H) 2.05-2.18 (m, 1H) 2.23-2.36 (m, 1H) 4.04 (s, 3H) 5.68-5.80 (m, 1H) 7.13 (d, J=4.29 Hz, 1H) 7.30 (d, J=8.08 Hz, 1H) 7.45-7.59 (m, 2H) 7.85 (d, J=8.08 Hz, 1H) 8.60 (s, 1H). [M+H] calc'd for C21H24N4O3S, 413; found, 413.

Workup

  1. customAll solvents were removed
  2. customThe crude product was purified via preparative HPLC

Sources & evidence

ORD record
ord-b01090ce8aac4989a71313daac587bbf
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Reaction notes

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