Dimethylamine → HCID 57904772, compound

HRID 1093113Notes

Reaction equation

HRID 1093113 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:14]([C:15](=[O:25])[C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][CH:12]1[CH2:26][CH2:27][C:9]2(OCC(O)=O)[CH2:10][CH2:11]1)=[O:5])[CH3:2].F[P-](F)(F)(F)(F)F.N1([O:49][C:50](N(C)C)=[N+:51]([CH3:53])[CH3:52])C2N=CC=CC=2N=N1.C1C[O:60][CH2:59]C1.CNC>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:13]2[N:14]([C:15](=[O:25])[C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:8][CH:9]1[CH2:10][CH2:11][C:12]2([O:60][CH2:59][C:50](=[O:49])[N:51]([CH3:53])[CH3:52])[CH2:26][CH2:27]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57905300HCID 57905300, compound

Product 1

HCID 57904772HCID 57904772, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-benzyloxy-1-carboxymethoxy-6-oxo-3,7-diazatricyclo[7.2.2.02,7]trideca-2,4-diene-4-carboxylic acid ethyl ester (25 mg, 0.057 mmol) in DMF (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (43 mg, 0.11 mmol) and 4-(dimethylamino)pyridine (DMAP) (14 mg, 0.11 mmol) and the mixture stirred at room temperature for 15 min under N2. To this was added a 2M THF solution of dimethylamine (0.057 mL, 0.11 mmol) and the mixture stirred at room temperature for 90 min. The mixture was concentrated and the residue taken up in ethyl acetate (10 mL), washed with 1N HCl followed by brine, then dried (Na2SO4) and concentrated to provide the title compound (36 mg, 0.057 mmol, 100% yield) as a crude amber film: HPLC: retention time=2.15 min; LCMS: m/z 470 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (3H, t, J=6.6 Hz), 1.65-1.76 (2H, m), 1.88-2.01 (2H, m), 2.11-2.26 (4H, m), 2.46 (1H, brs), 2.90 (3H, s), 2.95 (3H, s), 4.10 (2H, t, J=7.0 Hz), 4.23-4.33 (4H, m), 5.24 (2H, s), 7.27-7.38 (3H, m), 7.46 (2H, d, J=7.0 Hz).

Workup

  1. stirringthe mixture stirred at room temperature for 90 min
  2. concentrationThe mixture was concentrated
  3. washwashed with 1N HCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c7938bab8d0475fa0d287e1eef247dc
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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