Triethylamine → 7-Methoxy-3-{1-[6-(3-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74627Notes

Reaction equation

HRID 74627 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.Cl.[C:54]1([C:60]2[C:64]3[CH2:65][NH:66][CH2:67][CH2:68][C:63]=3[NH:62][N:61]=2)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C.CO>[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[CH2:37][CH2:38][N:39]([C:42]4[CH:43]=[C:44]([C:48]([N:66]5[CH2:67][CH2:68][C:63]6[NH:62][N:61]=[C:60]([C:54]7[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=7)[C:64]=6[CH2:65]5)=[O:50])[N:45]=[CH:46][N:47]=4)[CH2:40][CH2:41]3)[CH2:31][CH2:30][C:29]=2[CH:51]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 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 acidHCID 673374503-phenyl-1H,4H,5H,6H,7H-pyrazolo(4,3-c)pyridine dihydrochloride

Product 1

HCID 583866017-Methoxy-3-{1-[6-(3-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-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, 75 mg (0.28 mmol) 3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride, 120.0 μL (0.86 mmol) triethylamine in 0.9 mL DMF and 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-564765cab9fd450592f16f06169334fe
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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