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

HRID 1846548Notes

Reaction equation

HRID 1846548 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]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([O:30][C:31]2[CH:40]=[C:39]([CH3:41])[C:34]3[NH:35][C:36](=[O:38])[O:37][C:33]=3[CH:32]=2)[CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:29][O:28][C:26]1[N:25]=[C:24]([O:30][C:31]2[CH:40]=[C:39]([CH3:41])[C:34]3[NH:35][C:36](=[O:38])[O:37][C:33]=3[CH:32]=2)[CH:23]=[C:22]([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)[N:27]=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 866639146-(6-chloro-2-methoxypyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one

Product 1

HCID 462447606-{2-methoxy-6-[4-(7-methoxy-2-oxo-4,5-dihydro-1H-benzo[d][1,3]diazepin-3(2H)-yl)-piperidin-1-yl]pyrimidin-4-yloxy}-4-methylbenzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

45 mg (0.16 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 50 mg (0.15 mmol) 6-(6-chloro-2-methoxypyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one and 0.10 mL (0.57 mmol) DIPEA in 1.0 mL DMF were stirred for 3 h at 90° C. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were combined and freeze-dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing product
  3. customfreeze-dried

Sources & evidence

ORD record
ord-5bc9f6aef06a450db1de45c824f4109e
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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