Formic Acid → 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

HRID 469391Notes

Reaction equation

HRID 469391 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.[Cl:21][C:22]1[N:23]=[N:24][C:25](Cl)=[CH:26][C:27]=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.C(O)=O>CN(C=O)C.O>[Cl:21][C:22]1[N:23]=[N:24][C:25]([N:17]2[CH2:18][CH2:19][CH:14]([N:10]3[CH2:9][CH2:8][C:7]4[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[NH:12][C:11]3=[O:13])[CH2:15][CH2:16]2)=[CH:26][C:27]=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]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 81531DiisopropylethylamineHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 581811846-(3,6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

360 mg (1.31 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 480 mg (1.19 mmol) 6-(3.6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one and 0.300 mL (1.74 mmol) DIPEA were stirred in 3 mL DMF for 4 h at 100° C. Then the reaction mixture was cooled, combined with 0.5 mL formic acid and 15 mL water, the precipitate formed was suction filtered and dried. This was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. temperatureThen the reaction mixture was cooled
  2. customthe precipitate formed
  3. filtrationfiltered
  4. customdried
  5. customThis was purified by preparative HPLC-MS
  6. additionThe fractions containing the product
  7. customfreeze-dried

Sources & evidence

ORD record
ord-55bb1887634a4b4d97f41f3bf8605ee8
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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