Diisopropylethylamine → HCID 86653641, compound

HRID 2064806Notes

Reaction equation

HRID 2064806 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:23][C:24]1[S:25][C:26]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=2)=[C:27]([C:29]([OH:31])=O)[N:28]=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.CN(C=O)C>[NH2:23][C:24]1[S:25][C:26]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=2)=[C:27]([C:29]([N:40]2[C@H:41]([CH2:45][NH:46][C:47](=[O:52])[C:48]([F:50])([F:51])[F:49])[CH2:42][C@H:43]3[C@@H:39]2[CH2:44]3)=[O:31])[N:28]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 574371792-Amino-5-(3-fluorophenyl)-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 86653641HCID 86653641, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

TBTU (3.22 mmol, 1.05 eq) is added to a solution of 2-amino-5-(3-fluoro-phenyl)-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) and DMF (3.0 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 preparative TLC (DCM/MeOH 9/1) to give the desired product as an orange foam. LC-MS (acidic): tR=0.87 min; [M+H]+=429.1.

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 preparative TLC (DCM/MeOH 9/1)

Sources & evidence

ORD record
ord-da8c4d191279490da31973d694078a9b
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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