Diisopropylethylamine → HCID 58386695, compound

HRID 74699Notes

Reaction equation

HRID 74699 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][N:17]([C:20]4[N:25]=[CH:24][N:23]=[C:22]([C:26]([OH:28])=O)[CH:21]=4)[CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:29]=1.CC[N:32]([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])C.CN(C(ON1N=NC2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>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[CH2:15][CH2:16][N:17]([C:20]4[CH:21]=[C:22]([C:26]([N:32]5[CH2:33][C:35]6([CH2:7][CH2:29][CH2:3][CH2:4]6)[C:50]6[C:38](=[CH:48][CH:53]=[CH:52][CH:51]=6)[CH:36]5[CH3:37])=[O:28])[N:23]=[CH:24][N:25]=4)[CH2:18][CH2:19]3)[CH2:9][CH2:8][C:7]=2[CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 583866166-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 58386695HCID 58386695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

42 mg (0.11 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid and 25 mg (0.11 mmol) 1′-methyl-2′,3′-dihydro-1′H-spiro[cyclopentan-1,4′-isoquinoline hydrochloride in 63 μL (0.36 mmol) DIPEA and 1.0 mL DMF were combined with 39 mg (0.12 mmol) TBTU and the mixture was stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and partially evaporated down. The precipitate formed was suction filtered and dried. The filtrate was freeze-dried. The residue remaining was identical to the precipitate.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. custompartially evaporated down
  3. customThe precipitate formed
  4. filtrationfiltered
  5. customdried
  6. customThe filtrate was freeze-dried

Sources & evidence

ORD record
ord-ce8285932a854d76858bb10cb5376959
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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