Diisopropylethylamine → 3-{1-[6-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-methyl-pyrimidin-4-yl]-3-fluoro-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469442Notes

Reaction equation

HRID 469442 reaction equation
[F:1][CH:2]1[CH:7]([N:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:11]=3[NH:10][C:9]2=[O:21])[CH2:6][CH2:5][NH:4][CH2:3]1.Cl[C:23]1[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([C:30]([C:32]2[CH:42]=[C:41]([CH3:43])[C:35]3[N:36]([CH3:40])[C:37](=[O:39])[O:38][C:34]=3[CH:33]=2)=[O:31])[CH:24]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:40][N:36]1[C:35]2[C:41]([CH3:43])=[CH:42][C:32]([C:30]([C:25]3[N:26]=[C:27]([CH3:29])[N:28]=[C:23]([N:4]4[CH2:5][CH2:6][CH:7]([N:8]5[CH2:14][CH2:13][C:12]6[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:11]=6[NH:10][C:9]5=[O:21])[CH:2]([F:1])[CH2:3]4)[CH:24]=3)=[O:31])=[CH:33][C:34]=2[O:38][C:37]1=[O:39]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581811376-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-oneHCID 581811423-(3-Fluoro-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d]-[1,3]diazepin-2-one

Product 1

HCID 252680233-{1-[6-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-methyl-pyrimidin-4-yl]-3-fluoro-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

82 mg (0.28 mmol) 3-(3-fluoro-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d]-[1,3]diazepin-2-one, 85 mg (0.27 mmol) 6-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.10 mL (0.56 mmol) DIPEA were combined in 2 mL DMF and stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The fractions containing the product were combined and the organic solvent was evaporated down. The residue was neutralised with 4N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customthe organic solvent was evaporated down
  4. customthe precipitate formed
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-42ca0063fdbb4fe2b14b45f0a204c6bc
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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