Diisopropylethylamine → 7-Chloro-3-{1-[6-(3,4-dimethyl-2-oxo-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 469397Notes

Reaction equation

HRID 469397 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7](=[O:17])[N:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:21]1[N:26]=[CH:25][N:24]=[C:23]([C:27]([C:29]2[CH:39]=[C:38]([CH3:40])[C:32]3[N:33]([CH3:37])[C:34](=[O:36])[O:35][C:31]=3[CH:30]=2)=[O:28])[CH:22]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7](=[O:17])[N:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:21]4[CH:22]=[C:23]([C:27]([C:29]5[CH:39]=[C:38]([CH3:40])[C:32]6[N:33]([CH3:37])[C:34](=[O:36])[O:35][C:31]=6[CH:30]=5)=[O:28])[N:24]=[CH:25][N:26]=4)[CH2:13][CH2:12]3)[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 581811547-Chloro-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-oneHCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 252708137-Chloro-3-{1-[6-(3,4-dimethyl-2-oxo-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 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

56 mg (0.20 mmol) 7-chloro-3-piperidin-4-yl-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one, 61 mg (0.20 mmol) 6-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.070 mL (0.40 mmol) DIPEA were stirred overnight in 1.5 mL DMF at RT. The mixture was diluted with 1.5 mL MeOH, suction filtered, washed with DIPE and dried.

Workup

  1. filtrationfiltered
  2. washwashed with DIPE
  3. customdried

Sources & evidence

ORD record
ord-87ee4d103ee249f18ae0335496607b80
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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