Dimethylformamide → HCID 21078794, compound

HRID 1375243Notes

Reaction equation

HRID 1375243 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.[C:6]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)([OH:8])=O.[CH:18]1[CH:19]=[CH:20][C:21]2N(O)N=N[C:22]=2[CH:23]=1.CN(C(ON1[N:44]=[N:43][C:38]2[CH:39]=[CH:40]C=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52]CN(C(C)C)C(C)C.CN([CH:64]=[O:65])C>>[CH:1]1([CH2:4][NH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:23]3[CH:18]=[C:19]([C:64]4[O:65][C:38]([CH2:39][CH3:40])=[N:43][N:44]=4)[CH:20]=[CH:21][C:22]=3[CH3:52])=[CH:11][CH:10]=2)=[O:8])[CH2:3][CH2:2]1

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3121834-Carboxyphenylboronic AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 21078794HCID 21078794, compound

Procedure

(Cyclopropylmethyl)amine (470 mg, 6.0 mmol), 4-carboxyphenylboronic acid (1.0 g, 6.0 mmol), HOBT (810 mg, 6.0 mmol), HBTU (2.73 g, 7.2 mmol) and DIPEA (1.71 g, 7.2 mmol) were mixed in DMF (10 ml) and stirred at room temperature for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM and aqueous sodium bicarbonate. The organic phase was separated, washed with water and brine and dried (magnesium sulphate). The solvent was evaporated under vacuum and the residue purified on a silica flash column eluting with DCM/ethanol/ammonia (15:8:1 then 10:10:1), to give after evaporation of the solvents 4-[N-(cyclopropylmethyl)aminocarbonyl]phenylboronic acid (300 mg, 23%).

Workup

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM and aqueous sodium bicarbonate
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. dry with materialdried (magnesium sulphate)
  6. customThe solvent was evaporated under vacuum
  7. customthe residue purified on a silica flash column
  8. washeluting with DCM/ethanol/ammonia (15:8:1
  9. custom10:10:1), to give
  10. customafter evaporation of the solvents 4-[N-(cyclopropylmethyl)aminocarbonyl]phenylboronic acid (300 mg, 23%)

Sources & evidence

ORD record
ord-de003aabfacb4777878ba9838930ee22
Source dataset
uspto-grants-2007_01
Patent number
US07166623B2

Reaction notes

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