Triethylamine → 3-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-yl 6-(tert-butoxycarbonylamino)hexanoate

HRID 1422505Notes

Reaction equation

HRID 1422505 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[N:14]=[C:13]3[C:9]([N:10]=[CH:11][N:12]3[CH:15]([CH3:17])[CH3:16])=[C:8]([NH:18][CH2:19][CH2:20][C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=4)[NH:23][CH:22]=3)[N:7]=2)[C:3]2[CH:31]=[CH:32][CH:33]=[CH:34][C:2]1=2.[C:35]([O:39][C:40]([NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48](O)=[O:49])=[O:41])([CH3:38])([CH3:37])[CH3:36].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:35]([O:39][C:40]([NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:20][CH2:19][NH:18][C:8]1[N:7]=[C:6]([C:4]2[C:3]3[CH:31]=[CH:32][CH:33]=[CH:34][C:2]=3[S:1][CH:5]=2)[N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[CH:15]([CH3:17])[CH3:16])=[O:49])=[O:41])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594089233-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-ol

Product 1

HCID 594089113-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-yl 6-(tert-butoxycarbonylamino)hexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-ol (55.5 mg, 0.119 mmol) and 6-(tert-butoxycarbonylamino)hexanoic acid (30 mg, 0.113 mmol) in DMF (3 ml) was added Et3N (24 mg, 0.237 mmol) and HATU (90 mg, 0.237 mmol). The mixture was stirred at rt for 16 hr, and then was concentrated. Water was added and the reaction mixture was extracted with ethyl acetate. The organic fractions were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (0 to 5% MeOH in DCM eluant) to afford the title compound as an off-white solid.

Workup

  1. concentrationwas concentrated
  2. additionWater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0 to 5% MeOH in DCM eluant)

Sources & evidence

ORD record
ord-bb511b42ee544e5383c1f3c867cfd5db
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

Loading…