Dimethylamine → HCID 57635028, compound

HRID 2111327Notes

Reaction equation

HRID 2111327 reaction equation
[CH:1]1([N:7]2[CH2:13][CH2:12][C:11](=[O:14])[NH:10][C:9]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[C:22](OC)[CH:21]=4)=[N:18][C:8]2=3)[CH2:6][CH2:5][CH2:4]CC1.F[P-](F)(F)(F)(F)F.[CH3:38][N:39]([C:41](N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.[CH3:55]NC.[O:58]1CCC[CH2:59]1>C(N(CC)CC)C.ClCCl>[CH:1]1([N:7]2[CH2:13][CH2:12][C:11](=[O:14])[N:10]([CH3:55])[C:9]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([C:24]([N:39]([CH3:41])[CH3:38])=[O:25])=[CH:27][C:28]=4[O:58][CH3:59])=[N:18][C:8]2=3)[CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 68740138HCID 68740138, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 57635028HCID 57635028, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 0.047 g (0.00012 mole) of 4-(9-cyclohexyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-methoxy-benzoic acid (I-28a), 0.050 g (0.00013 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.1 mL (0.0002 mole) of 2M dimethylamine in tetrahydrofuran, 0.075 mL of triethylamine and 2 mL of dichloromethane was stirred overnight at ambient temperature. The mixture was diluted with 3 mL of dichloromethane, washed with 2.5 mL of 0.2 M sodium hydroxide. The dichloromethane layer was concentrated under reduced pressure, and the residue purified by C18 reverse phase silica gel chromatography, eluting with an acetonitrile-water gradient (10:90-100:0) to give 0.033 g of 4-(9-cyclobutyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N,N-dimethyl-benzamide (I-35)

Workup

  1. washwashed with 2.5 mL of 0.2 M sodium hydroxide
  2. concentrationThe dichloromethane layer was concentrated under reduced pressure
  3. customthe residue purified by C18 reverse phase silica gel chromatography
  4. washeluting with an acetonitrile-water gradient (10:90-100:0)

Sources & evidence

ORD record
ord-14c4dbd672234fc49694e9a180f4138e
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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