Diisopropylethylamine → 3-{1-[6-(2-cyclopropyl-4-methyl-1H-benzo[d]imidazol-6-yloxy)pyrimidin-4-yl]piperidin-4-yl}-7-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

HRID 1846550Notes

Reaction equation

HRID 1846550 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[C:22]1[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]2[CH:30]=[C:31]([CH3:41])[C:32]3[N:36]=[C:35]([CH:37]4[CH2:39][CH2:38]4)[NH:34][C:33]=3[CH:40]=2)[CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:37]1([C:35]2[NH:34][C:33]3[CH:40]=[C:29]([O:28][C:24]4[N:25]=[CH:26][N:27]=[C:22]([N:17]5[CH2:18][CH2:19][CH:14]([N:10]6[CH2:9][CH2:8][C:7]7[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=7[NH:12][C:11]6=[O:13])[CH2:15][CH2:16]5)[CH:23]=4)[CH:30]=[C:31]([CH3:41])[C:32]=3[N:36]=2)[CH2:38][CH2:39]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 866639156-(6-chloropyrimidin-4-yloxy)-2-cyclopropyl-4-methyl-1H-benzo[d]imidazole

Product 1

HCID 462447623-{1-[6-(2-cyclopropyl-4-methyl-1H-benzo[d]imidazol-6-yloxy)pyrimidin-4-yl]piperidin-4-yl}-7-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44 mg (0.16 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 40 mg (0.13 mmol) 6-(6-chloropyrimidin-4-yloxy)-2-cyclopropyl-4-methyl-1H-benzo[d]imidazole and 0.06 mL (0.32 mmol) DIPEA in 2.0 mL DMF were stirred overnight at RT. The reaction mixture was purified by preparative HPLC-MS. The fractions containing the product were partially evaporated down i.vac. and neutralised with 4M sodium hydroxide solution. The precipitate formed was suction filtered, washed and dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customwere partially evaporated down i.vac
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-5c9e204a76d0416aa947e9fefe1bbe7f
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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