Sodium Hydroxide → HCID 46243981, compound

HRID 1846577Notes

Reaction equation

HRID 1846577 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[NH:7][C:8](=[O:18])[N:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl[C:22]1[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]2[CH:30]=[C:31]([CH3:43])[C:32]3[N:36]=[C:35]([CH:37]4[CH2:41][CH2:40][O:39][CH2:38]4)[NH:34][C:33]=3[CH:42]=2)[CH:23]=1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[NH:7][C:8](=[O:18])[N:9]([CH:12]3[CH2:13][CH2:14][N:15]([C:22]4[CH:23]=[C:24]([O:28][C:29]5[CH:30]=[C:31]([CH3:43])[C:32]6[N:36]=[C:35]([CH:37]7[CH2:41][CH2:40][O:39][CH2:38]7)[NH:34][C:33]=6[CH:42]=5)[N:25]=[CH:26][N:27]=4)[CH2:16][CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 86663933HCID 86663933, compound

Product 1

HCID 46243981HCID 46243981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 mg (0.10 mmol) 7-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one, 33 mg (0.10 mmol) 6-(6-chloropyrimidin-4-yloxy)-4-methyl-2-(tetrahydrofuran-3-yl)-1H-benzo[d]imidazole and 30 μL (0.20 mmol) DIPEA in 2.0 mL DMF were stirred at 50° C. over the weekend. The reaction mixture was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 4 M aqueous NaOH solution. The precipitate formed was suction filtered, washed and dried.

Workup

  1. customThe reaction mixture was purified by chromatography
  2. additionThe fractions containing product
  3. customevaporated down i.vac
  4. customto leave the aqueous residue
  5. customThe precipitate formed
  6. filtrationfiltered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-daf23a999f334fb7bf756c39dfef84a4
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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