O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 4'-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carbonyl)-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile

HRID 74649Notes

Reaction equation

HRID 74649 reaction equation
[C:1]([C:3]1[C:4]([C:29](O)=[O:30])=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:21][CH2:20][C:19]4[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=4[NH:17][C:16]3=[O:28])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)#[N:2].Cl.Cl.[CH3:34][C:35]1([CH3:44])[CH2:40][NH:39][CH2:38][C:37]2[CH:41]=[N:42][NH:43][C:36]1=2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:34][C:35]1([CH3:44])[CH2:40][N:39]([C:29]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([N:9]3[CH2:14][CH2:13][CH:12]([N:15]4[CH2:21][CH2:20][C:19]5[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=5[NH:17][C:16]4=[O:28])[CH2:11][CH2:10]3)[CH:5]=2)=[O:30])[CH2:38][C:37]2[CH:41]=[N:42][NH:43][C:36]1=2

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58386480HCID 58386480, compoundHCID 667221937,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride

Product 1

HCID 583865744'-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carbonyl)-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.24 mmol) 5′-cyano-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid, 53.2 mg (0.24 mmol) 7,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride, 137 μL (0.97 mmol) TEA and 83.8 mg (0.26 mmol) TBTU were stirred in 2 mL DMF overnight at RT. The reaction mixture was purified by HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-1ae4d5aa39a14811a0dd9a7860b702c2
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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