Diisopropylethylamine → 7-Methoxy-3-{-1-[6-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylamino)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 1846523Notes

Reaction equation

HRID 1846523 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]([NH:28][C:29]2[CH:38]=[C:37]([CH3:39])[C:32]3[NH:33][C:34](=[O:36])[O:35][C:31]=3[CH:30]=2)[CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[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][N:17]([C:22]4[CH:23]=[C:24]([NH:28][C:29]5[CH:38]=[C:37]([CH3:39])[C:32]6[NH:33][C:34](=[O:36])[O:35][C:31]=6[CH:30]=5)[N:25]=[CH:26][N:27]=4)[CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=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 866638946-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 462442257-Methoxy-3-{-1-[6-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylamino)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg (0.29 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 90 mg (0.26 mmol) 6-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one and 0.15 mL (0.87 mmol) DIPEA in 1.5 mL DMF were stirred at 150° C. After the reaction of the reactants the reaction mixture was purified by preparative HPLC. The product-containing fractions were combined and evaporated down. The residue was dried.

Workup

  1. customAfter the reaction of the reactants the reaction mixture
  2. customwas purified by preparative HPLC
  3. customevaporated down
  4. customThe residue was dried

Sources & evidence

ORD record
ord-54b8b6798c1c47b396dcdf60797dc0fb
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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