Methanol → 7-Methoxy-3-{1-[5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469380Notes

Reaction equation

HRID 469380 reaction equation
[OH:1][CH:2]([C:29]1[CH:38]=[C:37]([CH3:39])[C:32]2[NH:33][C:34](=[O:36])[O:35][C:31]=2[CH:30]=1)[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:21][CH2:20][C:19]4[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=4[NH:17][C:16]3=[O:28])[CH2:11][CH2:10]2)[N:6]=[N:7][CH:8]=1.CO>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:18]2[NH:17][C:16](=[O:28])[N:15]([CH:12]3[CH2:11][CH2:10][N:9]([C:5]4[N:6]=[N:7][CH:8]=[C:3]([C:2]([C:29]5[CH:38]=[C:37]([CH3:39])[C:32]6[NH:33][C:34](=[O:36])[O:35][C:31]=6[CH:30]=5)=[O:1])[CH:4]=4)[CH2:14][CH2:13]3)[CH2:21][CH2:20][C:19]=2[CH:22]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 581810963-(1-{5-[Hydroxy-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-methyl]-pyridazin-3-yl}-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Product 1

HCID 252687407-Methoxy-3-{1-[5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

0.13 g (0.049 mmol) 3-(1-{5-[hydroxy-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-methyl]-pyridazin-3-yl}-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one and 1.0 g (12 mmol) manganese(IV)-oxide in 100 mL DCM were stirred overnight at RT. Then 500 mg manganese(IV)-oxide were added and the mixture was stirred for a further 20 h. Then the reaction mixture was combined with 10 mL MeOH, filtered off and evaporated down. The residue was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. filtrationfiltered off
  2. customevaporated down
  3. customThe residue was purified by preparative HPLC-MS
  4. additionThe fractions containing the product
  5. customfreeze-dried

Sources & evidence

ORD record
ord-66f1fb55209e4adeac12df80d95cbd91
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

Loading…