1-Hydroxybenzotriazole → HCID 86691460, compound

HRID 1618864Notes

Reaction equation

HRID 1618864 reaction equation
[CH:1](=[C:3]1[C:7]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[O:17][CH2:18][C:19](O)=[O:20])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH:5]([CH3:25])[N:4]1[CH3:26])[CH3:2].[C:27]([NH:34][CH2:35][CH2:36][NH2:37])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(#N)C>[CH:1](=[C:3]1[C:7]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[O:17][CH2:18][C:19]([NH:37][CH2:36][CH2:35][NH:34][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:20])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH:5]([CH3:25])[N:4]1[CH3:26])[CH3:2]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86691461HCID 86691461, compound

Product 1

HCID 86691460HCID 86691460, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

Product of Step 11 (0.11 g) was dissolved in acetonitrile (10 mL). To this, N-boc-ethylene diamine (0.1 g), HBTU (0.4 g), HOBT (0.15 g), and DIPEA (1 mL) were added. The reaction mixture was stirred at 25° C. for 1 hr and was evaporated under vacuum. Residue was dissolved in dichloromethane (300 mL) and was extracted with water (twice at 200 mL each). The organic layer was dried on anhydrous magnesium sulfate and was filtered and was evaporated. Crude product was loaded on a SNAP cartridge containing 100 g silica gel and eluted with a gradient of chloroform and methanol using the BIOTAGE® AB ISOLERA™ flash chromatography system. Fractions containing product were pooled and evaporated under vacuum to obtain Step 12 (0.13 g). 1H NMR (CDCl3): 1.25 δ (—CH—CH3 of isopropyl), 1.5 δ (9H, —(CH3)3 of N-boc) 1.8 δ (3H, ═CH—CH3 of ethylidene) 2.9 δ (3H, —N—(CH3)), 2.2, 2.3, 3.1 δ (1H, 1H, 1H —CH2-CH—CH3 of isopropyl), 3.3, 3.5 δ (2H, 2H, —N—CH2-CH2-N—), 4.4 δ (1H, ═CH—CH3 of ethylidene), 4.5 (2H, —O—CH2-C(O)—), 6.8-7.5 δ (9H, phenyl rings). Mass spectrometry: m/z=494 (M+H).

Workup

  1. customwas evaporated under vacuum
  2. dissolutionResidue was dissolved in dichloromethane (300 mL)
  3. extractionwas extracted with water (twice at 200 mL each)
  4. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. customwas evaporated
  7. additioncontaining 100 g silica gel
  8. washeluted with a gradient of chloroform and methanol using the BIOTAGE® AB ISOLERA™ flash chromatography system
  9. additionFractions containing product
  10. customevaporated under vacuum
  11. customto obtain Step 12 (0.13 g)

Sources & evidence

ORD record
ord-f381da20abbc4bad8f253603c2975997
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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