Dimethylformamide → HCID 24759086, compound

HRID 1672386Notes

Reaction equation

HRID 1672386 reaction equation
[CH2:1]([N:8]1[CH:14]([C:15]([OH:17])=O)[CH2:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>>[CH2:1]([N:8]1[CH:14]([C:15]([NH:29][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:17])[CH2:13][C:10]2([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7965CyclohexylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67355077HCID 67355077, compound

Product 1

HCID 24759086HCID 24759086, compound

Procedure

To a mixture of 5-benzyl-5-azaspiro[2.4]heptane-6-carboxylic acid (62.0 mg, 0.000268 mol) dissolved in DMF (1.0 mL, 0.013 mol) was added cyclohexanamine (30.7 μL, 0.000268 mol), benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (130 mg, 0.00029 mol) and TEA (0.25 mL, 0.0018 mol). After stirring at RT for 1 h, the reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The extracts were washed with brine, then dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by prep.-LC/MS to afford the desired product as a white solid. LC/MS: m/e 313.2 (M+1H)+.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by prep.-LC/MS

Sources & evidence

ORD record
ord-880e51bf71834ab3be69c2691059f6f5
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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