Diisopropylethylamine → Tert-butyl 2-(2-(4-(3-azidopropylamino)-6-(2-hydroxyethylamino)-1,3,5-triazin-2-ylamino)ethoxy)ethylcarbamate

HRID 1404417Notes

Reaction equation

CC[N:3](C(C)C)C(C)C.NCCO[CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].[N:27]([CH2:30][CH2:31][CH2:32][NH:33][C:34]1[N:39]=[C:38](Cl)[N:37]=[C:36]([NH:41][CH2:42][CH2:43][OH:44])[N:35]=1)=[N+:28]=[N-:29]>C1COCC1>[N:27]([CH2:30][CH2:31][CH2:32][NH:33][C:34]1[N:35]=[C:36]([NH:41][CH2:42][CH2:43][OH:44])[N:37]=[C:38]([NH:3][CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[N:39]=1)=[N+:28]=[N-:29]

Participants

Conditions

Temperature: 70 °C

Procedure

DIPEA (142 mg, 1.10 mmol), tert-butyl 2-(2-(2-aminoethoxy)ethoxy)ethylcarbamate (273 mg, 1.10 mmol), and 2 (150 mg, 0.55 mmol) were dissolved in THF (5 mL). The mixture was stirred at 70° C. under N2 overnight. The solvent was removed under reduced pressure. The resulting residue was purified by column chromatography on silica gel (eluent CH3OH/CH2Cl2=2/98) to give 3 as a white solid (124 mg, 47%): ESI-MS m/z 485.2 (M+H+) calculated for C19H37N10O5 485.3.

Workup

customThe solvent was removed under reduced pressure
customThe resulting residue was purified by column chromatography on silica gel (eluent CH3OH/CH2Cl2=2/98)

Sources & evidence

ORD record: ord-0f7cfccab33445ac85b318cebb04b4b6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912323B2

Reaction notes

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