Diisopropylethylamine → HCID 131733557, compound

HRID 1747214Notes

Reaction equation

HRID 1747214 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C@@H:6]1[CH2:11][O:10][CH2:9][CH2:8][NH:7]1.CCN(C(C)C)C(C)C.[N:24]1[N:25]([C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31](O)=[O:32])[N:26]=[CH:27][CH:28]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C@@H:6]1[CH2:11][O:10][CH2:9][CH2:8][N:7]1[C:31]([C:30]1[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=1[N:25]1[N:26]=[CH:27][CH:28]=[N:24]1)=[O:32]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acidHCID 118117228HCID 118117228, compound

Product 1

HCID 131733557HCID 131733557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (R)-3-(3-iodo-benzyl)-morpholine B-5 (100 mg, 0.33 mmol) and DIPEA (57 μL, 0.33 mmol) in DMF (1.5 mL) was added to a RT solution of 2-(2H-1,2,3-triazol-2-yl)benzoic acid E-2 (62 mg, 0.33 mmol), TBTU (111 mg, 0.35 mmol) and DIPEA (57 μL, 0.33 mmol) in DMF (1.5 ml) under argon and the resulting mixture was stirred for 22 h. The reaction mixture was quenched with sat. aq. NaHCO3 and stirred for 10 min before being diluted with water and extracted with DCM (3×). The combined organic extracts were washed with 2M aq. NaOH (1×), 2M aq. HCl (1×) and brine (1×), dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by prep. HPLC (method F) to give the title compound as a white solid. LC-MS D: tR=0.93 min; [M+H]+=474.91.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NaHCO3
  2. stirringstirred for 10 min
  3. additionbefore being diluted with water
  4. extractionextracted with DCM (3×)
  5. washThe combined organic extracts were washed with 2M aq. NaOH (1×), 2M aq. HCl (1×) and brine (1×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-8c9c3434ef50430fb9fe8cfe67728883
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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