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Diisopropylethylamine → HCID 58386517, compound

HRID 74652
Notes
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Reaction equation

HRID 74652 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]([N:30]2[CH:38]3[CH:33]([CH2:34][CH2:35][CH2:36][CH2:37]3)[CH2:32][CH2:31]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]([N:30]5[CH:38]6[CH:33]([CH2:34][CH2:35][CH2:36][CH2:37]6)[CH2:32][CH2:31]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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 58386728(6-Chloropyrimidin-4-yl)-(octahydroindol-1-yl)-methanone

Product 1

HCID 58386517HCID 58386517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

705 mg (2.56 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 680 mg (2.56 mmol) (6-chloro-pyrimidin-4-yl)-(octahydro-indol-1-yl)-methanone and 0.871 mL (5 mmol) DIPEA were stirred in 10 mL DMF for 2 h at RT. The reaction mixture was purified by HPLC. The product-containing fractions were combined and the ACN was eliminated by rotary evaporation. The aqueous phase was made alkaline with 4M NaOH and extracted with EtOAc. The organic phase was dried, filtered and the filtrate was concentrated to dryness by rotary evaporation. The residue was crystallised from a mixture of MeOH and diethyl ether and the solid was suction filtered and dried.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. customthe ACN was eliminated by rotary evaporation
  3. extractionextracted with EtOAc
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to dryness by rotary evaporation
  7. customThe residue was crystallised from a mixture of MeOH and diethyl ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-441a4bff0ea9403996c1db01ffb535b0
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes