Methanol → 7-Methoxy-3-{1-[6-methoxy-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 469384Notes

Reaction equation

HRID 469384 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=4[NH:16][C:15]3=[O:27])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:28]([C:30]1[CH:39]=[C:38]([CH3:40])[C:33]2[NH:34][C:35](=[O:37])[O:36][C:32]=2[CH:31]=1)=[O:29].CCN(C(C)C)C(C)C.CO.C[C:53](C)([O-:55])C.[K+]>C(O)(=O)C>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:17]2[NH:16][C:15](=[O:27])[N:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:5]4[N:6]=[N:7][C:2]([O:55][CH3:53])=[C:3]([C:28]([C:30]5[CH:39]=[C:38]([CH3:40])[C:33]6[NH:34][C:35](=[O:37])[O:36][C:32]=6[CH:31]=5)=[O:29])[CH:4]=4)[CH2:9][CH2:10]3)[CH2:20][CH2:19][C:18]=2[CH:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 23665647Potassium tert-butoxideHCID 252694613-{1-[6-Chloro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Product 1

HCID 252690997-Methoxy-3-{1-[6-methoxy-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 1

HCID 176Acetic AcidSolvent

Procedure

0.13 g (0.11 mmol) (purity 50%) 3-{1-[6-chloro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]-diazepin-2-one and 0.050 mL (0.29 mmol) DIPEA were heated with 1 mL MeOH in a microwave container for 2 h at 125° C. Then potassium-tert-butoxide was added and the mixture was stirred for 48 h at RT. Next, the reaction mixture was heated for a further 6 h and then it was neutralised with acetic acid and purified by preparative HPLC-MS.

Workup

  1. temperatureNext, the reaction mixture was heated for a further 6 h
  2. custompurified by preparative HPLC-MS

Sources & evidence

ORD record
ord-bda02f9cc2f648ae9f614542fa30dcda
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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