Triethylamine → 3-{1-[6-(3-bromo-7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74531Notes

Reaction equation

HRID 74531 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[NH:34][C:33](=[O:35])[N:32]([CH:36]3[CH2:41][CH2:40][N:39]([C:42]4[N:47]=[CH:46][N:45]=[C:44]([C:48]([OH:50])=O)[CH:43]=4)[CH2:38][CH2:37]3)[CH2:31][CH2:30][C:29]=2[CH:51]=1.Cl.[Br:53][C:54]1[CH:55]=[N:56][C:57]2[CH2:58][CH2:59][NH:60][CH2:61][C:62]=2[CH:63]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C.CO>[Br:53][C:54]1[CH:55]=[N:56][C:57]2[CH2:58][CH2:59][N:60]([C:48]([C:44]3[N:45]=[CH:46][N:47]=[C:42]([N:39]4[CH2:40][CH2:41][CH:36]([N:32]5[CH2:31][CH2:30][C:29]6[CH:51]=[C:25]([O:24][CH3:23])[CH:26]=[CH:27][C:28]=6[NH:34][C:33]5=[O:35])[CH2:37][CH2:38]4)[CH:43]=3)=[O:50])[CH2:61][C:62]=2[CH:63]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 441183183-Bromo-5,6,7,8-Tetrahydro-1,6-Naphthyridine HydrochlorideHCID 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 583866353-{1-[6-(3-bromo-7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

90 mg (0.24 mmol) TBTU were added to 80 mg (0.20 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 70 mg (0.28 mmol) 3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine-hydrochloride and 120 μL (0.86 mmol) triethylamine in 0.9 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was combined with 1 mL methanol, 1 mL saturated sodium hydrogen carbonate solution and 8 mL ice water. The precipitate was suction filtered, washed with water and diethyl ether and dried.

Workup

  1. filtrationfiltered
  2. washwashed with water and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-b70e74d8086443b0a3f5d89d53d894a4
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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