Diisopropylethylamine → HCID 86700517, compound

HRID 1500527Notes

Reaction equation

HRID 1500527 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[C:8]1[N:9]=[C:10]([C@@H:12]3[CH2:16][C@H:15]([CH3:17])[CH2:14][NH:13]3)[NH:11][C:7]=1[CH:6]=[CH:5]2.[CH3:21][O:22][C:23]([NH:25][C@@H:26]([CH:30]([CH3:32])[CH3:31])[C:27](O)=[O:28])=[O:24].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:21][O:22][C:23](=[O:24])[NH:25][C@H:26]([C:27]([N:13]1[CH2:14][C@@H:15]([CH3:17])[CH2:16][C@H:12]1[C:10]1[NH:11][C:7]2[CH:6]=[CH:5][C:4]3[C:18](=[CH:19][CH:20]=[C:2]([Br:1])[CH:3]=3)[C:8]=2[N:9]=1)=[O:28])[CH:30]([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 86700518HCID 86700518, compound

Product 1

HCID 86700517HCID 86700517, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-2-((2S,4S)-4-methyl-pyrrolidin-2-yl)-3H-naphtho[1,2-d]imidazole (1.05 g, 3.2 mmol; Preparation 27) in DCM (20 mL) was added (S)-2-methoxycarbonylamino-3-methyl-butyric acid (672 mg, 3.84 mmol), DIPEA (825 mg, 6.4 mmol), and HATU (1.82 g, 4.8 mmol). The reaction mixture was stirred at RT for 4 h and extracted with DCM (3×250 mL). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography (1:1 EtOAc:petroleum ether) to provide the title intermediate (1.2 g) (m/z): [M+H]+ calcd for C23H27BrN4O3 487.13, 489.12 found 489.2.

Workup

  1. extractionextracted with DCM (3×250 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (1:1 EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-d073e6b612d84e55b41d5dafc518363e
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

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