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

HRID 469426Notes

Reaction equation

HRID 469426 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]([C:28]([C:30]2[CH:40]=[C:39]([CH2:41][N:42]3[CH:46]=[CH:45][CH:44]=[N:43]3)[C:33]3[N:34]([CH3:38])[C:35](=[O:37])[O:36][C:32]=3[CH:31]=2)=[O:29])[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]([C:28]([C:30]5[CH:40]=[C:39]([CH2:41][N:42]6[CH:46]=[CH:45][CH:44]=[N:43]6)[C:33]6[N:34]([CH3:38])[C:35](=[O:37])[O:36][C:32]=6[CH:31]=5)=[O:29])[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 581812156-(6-chloro-pyrimidine-4-carbonyl)-3-methyl-4-pyrazol-1-ylmethyl-3H-benzoxazol-2-one

Product 1

HCID 252666227-Methoxy-3-{1-[6-(3-methyl-2-oxo-4-pyrazol-1-ylmethyl-2,3-dihydro-benzoxazole-6-carbonyl)-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

140 mg (0.508 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 210 mg (0.284 mmol) 6-(6-chloro-pyrimidine-4-carbonyl)-3-methyl-4-pyrazol-1-ylmethyl-3H-benzoxazol-2-one and 0.100 mL (0.581 mmol) DIPEA were combined in 1.0 mL DMF and stirred for 48 h at RT. Then the reaction mixture was purified several times by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. customThen the reaction mixture was purified several times by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customfreeze-dried

Sources & evidence

ORD record
ord-0ce944430cfc49f4ad46d624d42f11d2
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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