Diisopropylethylamine → HCID 86653640, compound

HRID 2064805Notes

Reaction equation

HRID 2064805 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:25]=[C:26]([C:30]2[S:34][C:33]([CH3:35])=[N:32][C:31]=2[C:36]([OH:38])=O)[CH:27]=[CH:28][CH:29]=1.[C@H:39]12[CH2:44][C@H:43]1[CH2:42][C@@H:41]([CH2:45][NH:46][C:47](=[O:52])[C:48]([F:51])([F:50])[F:49])[NH:40]2.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:51][C:48]([F:49])([F:50])[C:47]([NH:46][CH2:45][C@@H:41]1[CH2:42][C@H:43]2[C@H:39]([CH2:44]2)[N:40]1[C:36]([C:31]1[N:32]=[C:33]([CH3:35])[S:34][C:30]=1[C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=1)=[O:38])=[O:52]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 574371745-(3-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acidHCID 86653639N-[(1S,3S,5S)-2-Azabicyclo[3.1.0]hex-3-ylmethyl]-2,2,2-trifluoroacetamide

Product 1

HCID 86653640HCID 86653640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TBTU (3.22 mmol, 1.05 eq) is added to a solution of 5-(3-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid (3.07 mmol, 1.0 eq), N-[(1S,3S,5S)-2-aza-bicyclo[3.1.0]hex-3-ylmethyl]-2,2,2-trifluoro-acetamide (3.07 mmol, 1.0 eq) and DIPEA (9.20 mmol, 3.0 eq) in DCM (15 mL). After 2 h the mixture is washed twice with water, once with sat. aqueous NaHCO3 solution, once with hydrochloric acid (0.2 M) and three times with water. The organic layer is dried over Na2SO4, the solvents are removed in vacuo and the residue is purified by flash chromatography (gradient: DCM to DCM/MeOH 19/1) and preparative TLC (DCM/MeOH 19/1) to give the desired product as an orange foam. LC-MS (acidic): tR=0.97 min; [M+H]+=428.1.

Workup

  1. washAfter 2 h the mixture is washed twice with water, once with sat. aqueous NaHCO3 solution, once with hydrochloric acid (0.2 M) and three times with water
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customthe solvents are removed in vacuo
  4. customthe residue is purified by flash chromatography (gradient: DCM to DCM/MeOH 19/1) and preparative TLC (DCM/MeOH 19/1)

Sources & evidence

ORD record
ord-2fa06ed99f41441789435e449d96642c
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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