Isopropanol → HCID 46852601, compound

HRID 1402740Notes

Reaction equation

HRID 1402740 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:17][N:16]([C:18]([O:20]C4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH2:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][NH:31]1.CCN(C(C)C)C(C)C.C(O)(C)C>ClCCCl.ClCCl>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:15][N:16]([C:18]([N:31]4[CH2:32][CH2:33][C:34]5[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:30]4)=[O:20])[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 70461,2,3,4-TetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 66739642HCID 66739642, compound

Product 1

HCID 46852601HCID 46852601, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl 3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidine-1-carboxylate (50 mg, 0.12 mmol), 1,2,3,4-tetrahydroisoquinoline (25 μl, 0.19 mmol) and DIPEA (42 μl, 0.24 mmol) were stirred in 1,2-dichloroethane (2 ml) and isopropanol (1 ml) at 120° C. in a sealed tube for 16 hrs. The mixture was then cooled to RT, diluted with dichloromethane (30 ml) and washed with 1M aq. K2CO3 (2×15 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by silica FCC (eluting with 99:1:1 to 92:8:1 gradient of DCM/MeOH/2M NH3 in MeOH) to give the title compound (9 mg, 19% yield) as colourless oil.

Workup

  1. washwashed with 1M aq. K2CO3 (2×15 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by silica FCC (eluting with 99:1:1 to 92:8:1 gradient of DCM/MeOH/2M NH3 in MeOH)

Sources & evidence

ORD record
ord-7ba24e4d55924a90bf00826679f47ba8
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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