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

HRID 1846554Notes

Reaction equation

HRID 1846554 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:38]=[CH:37][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[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]5[CH:38]=[CH:37][C:32]6[NH:33][C:34](=[O:36])[O:35][C:31]=6[CH:30]=5)[CH:23]=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 86663917HCID 86663917, compound

Product 1

HCID 462448536-(6-(4-(7-methoxy-2-oxo-4,5-dihydro-1H-benzo[d][1,3]diazepin-3(2H)-yl)piperidin-1-yl)pyrimidin-4-yloxy)benzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.36 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 90 mg (0.34 mmol) 6-(6-chloropyrimidin-4-yloxy)benzo[d]oxazol-2(3H)-one and 0.07 mL (0.41 mmol) DIPEA in 2.0 mL DMF were stirred overnight at RT and for 4 h at 40° C. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were partially evaporated down i.vac. The precipitate formed was suction filtered, washed and dried.

Workup

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

Sources & evidence

ORD record
ord-6b26f4bd6d8c41f7a8b1953700c65f84
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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