Isopropylamine → HCID 57635431, compound

HRID 1971118Notes

Reaction equation

HRID 1971118 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C@H:3]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]2[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[CH2:15][C:14]=12)=[O:9])[C:4](O)=[O:5].[CH:29]([NH2:32])([CH3:31])[CH3:30].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH:29]([NH:32][C:4](=[O:5])[C@@H:3]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:13]2[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[CH2:15][C:14]=12)=[O:9])[C:2]([CH3:27])([CH3:28])[CH3:1])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57635204HCID 57635204, compound

Product 1

HCID 57635431HCID 57635431, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound 471 (30 mg, 0.078 mmol) and isopropylamine (33 μL, 0.39 mmol) in DMF was added TBTU (38 mg, 0.15 mmol). After stirring at room temperature overnight, the crude reaction mixture was purified by a prep LC-MS with 5% to 95% MeCN/water in 15 min to give pure Compound 472 at 66% yield. 1H-NMR (400 MHz, CDCl3) δ: 1.04 (s, 9H), 1.11-1.28 (m, 6H), 1.95 9 (br, 2H) 2.59 (s, 3H), 3.25 (br, 2H), 4.01-4.16 (m, 1H), 4.23 (d, J=9.3 Hz, 1H), 5.80 (br, 1H), 7.47-7.55 (m, 5H), 7.95 (d, J=9.3 Hz, 1H). LCMS (+ESI) m/z 426.0 [M+H]+.

Workup

  1. customthe crude reaction mixture
  2. customwas purified by a prep LC-MS with 5% to 95% MeCN/water in 15 min

Sources & evidence

ORD record
ord-47101c6b1539480aa6d41daf0eaa58b8
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

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