Tert-Butylamine → HCID 53247316, compound

HRID 1748361Notes

Reaction equation

HRID 1748361 reaction equation
[CH3:1][C:2]1([CH3:28])[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([NH:17][C:18]4[N:19]=[C:20]([C:24]([OH:26])=O)[N:21]([CH3:23])[CH:22]=4)=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:27])[NH:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[C:50]([NH2:54])([CH3:53])([CH3:52])[CH3:51].C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:50]([NH:54][C:24]([C:20]1[N:21]([CH3:23])[CH:22]=[C:18]([NH:17][C:15]([C:10]2[CH:11]=[CH:12][C:13]3[CH:14]=[C:6]4[C:5](=[O:27])[NH:4][CH2:3][C:2]([CH3:28])([CH3:1])[N:7]4[C:8]=3[CH:9]=2)=[O:16])[N:19]=1)=[O:26])([CH3:53])([CH3:52])[CH3:51]

Participants

8

Reactant 5

HCID 6385Tert-ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67235348HCID 67235348, compound

Product 1

HCID 53247316HCID 53247316, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{[(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indol-7-yl)carbonyl]amino}-1-methyl-1H-imidazole-2-carboxylic acid (104 mg, 0.27 mmol) in DMF (2 mL) are added N-hydroxybenzotriazole (74 mg, 0.55 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (105 mg, 0.55 mmol). After stifling for 10 min at 50° C., tert-butylamine (0.06 mL, 0.55 mmol), N,N-diisopropylethylamine (0.10 mL, 0.55 mmol) and 4-dimethylaminopyridine (6.7 mg, 0.06 mmol) are added. The reaction mixture is stirred at room temperature for 8 h. The solvent is removed under N2 stream to afford the crude compound which is purified by flash column chromatography to afford the title compound (61 mg, 51%). LCMS (ESMS): m/z 437.78 (M+H+).

Workup

  1. customThe solvent is removed under N2 stream
  2. customto afford the crude compound which
  3. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-38277d337d5243a1a7cae576e44f637b
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…