NoName_3327 → 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid(1H-indazol-4-yl)-amide

HRID 74695

Reaction equation

HRID 74695 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[NH:7][C:8](=[O:27])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([C:24]([OH:26])=O)C=C[N:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[NH2:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1[CH:33]=[N:34][NH:35]2.[CH3:40][N:41](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH:35]1[C:36]2[C:32](=[C:31]([NH:30][C:24]([C:22]3[CH:23]=[C:18]([N:15]4[CH2:16][CH2:17][CH:12]([N:9]5[CH2:10][CH2:11][C:5]6[CH:4]=[C:3]([O:2][CH3:1])[CH:29]=[CH:28][C:6]=6[NH:7][C:8]5=[O:27])[CH2:13][CH2:14]4)[N:19]=[CH:40][N:41]=3)=[O:26])[CH:39]=[CH:38][CH:37]=2)[CH:33]=[N:34]1

Participants

5

Reactant 3

HCID 413085NoName_3327HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 583864334-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid

Product 1

HCID 426132236-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid(1H-indazol-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.25 mmol) 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid and 34 mg (0.25 mmol) 4-amino-indazole in 74 mμL (0.53 mmol) TEA and 1.5 mL DMF were combined with 89 mg (0.28 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 freeze-dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customfreeze-dried

Sources & evidence

ORD record
ord-2832dc2c146b469cb93d3bc6b833b7f1
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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