Isopropylamine → HCID 44419211, compound

HRID 1364556Notes

Reaction equation

HRID 1364556 reaction equation
[CH3:1][S:2]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([NH2:19])[C:16]([C:20]#[N:21])=[C:15](Cl)[N:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:25]([NH2:28])([CH3:27])[CH3:26]>CN(C)C(=O)C.C(#N)C>[NH2:19][C:17]1[C:16]([C:20]#[N:21])=[C:15]([NH:28][CH:25]([CH3:27])[CH3:26])[N:14]=[C:13]([C:11]([NH:10][CH2:9][C:8]2[CH:23]=[CH:24][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[O:12])[CH:18]=1

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 23647238HCID 23647238, compound

Product 1

HCID 44419211HCID 44419211, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of Example 181F (36 mg, 0.1 mmol), isopropylamine (85 μL, 1.0 mmol) in N,N-dimethylacetamide (500 μL) was heated at 190° C. for 80 minutes in a microwave reactor. The crude mixture was diluted with 1 mL acetonitrile and purified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate), followed by second purification via silica gel chromatography, eluting with hexane/ethyl acetate (1:1 to 100% ethyl acetate) to provide the titled compound (8 mg, 21% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.02 (t, J=6.4 Hz, 1H), 7.88 (d, J=8.5 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 6.89 (bs, 2H), 6.69 (s, 1H), 6.15 (d, J=8.1, 1H), 4.58-4.46 (m, 3H), 3.17 (s, 3H), 1.16 (t, J=6.8 Hz, 6H). MS (m/e) 388 (M+H)+.

Workup

  1. custompurified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate)
  2. customfollowed by second purification via silica gel chromatography
  3. washeluting with hexane/ethyl acetate (1:1 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-78a123b433a741f1ade63b0ea27f9028
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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