O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 42612978, compound

HRID 74677Notes

Reaction equation

HRID 74677 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](O)=[O:49])[CH:43]=4)[CH2:38][CH2:37]3)[CH2:31][CH2:30][C:29]=2[CH:51]=1.Cl.[CH3:53][C:54]1([CH3:67])[CH2:59][NH:58][CH2:57][C:56]2[C:60]([C:63]([F:66])([F:65])[F:64])=[N:61][NH:62][C:55]1=2>CN(C=O)C>[CH3:53][C:54]1([CH3:67])[CH2:59][N:58]([C:48]([C:44]2[N:45]=[CH:46][N:47]=[C:42]([N:39]3[CH2:38][CH2:37][CH:36]([N:32]4[CH2:31][CH2:30][C:29]5[CH:51]=[C:25]([O:24][CH3:23])[CH:26]=[CH:27][C:28]=5[NH:34][C:33]4=[O:35])[CH2:41][CH2:40]3)[CH:43]=2)=[O:49])[CH2:57][C:56]2[C:60]([C:63]([F:66])([F:64])[F:65])=[N:61][NH:62][C:55]1=2

Participants

5

Reactant 3

HCID 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 67338170HCID 67338170, compound

Product 1

HCID 42612978HCID 42612978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.11 g (0.28 mmol) TBTU were added to 0.10 g (0.25 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 90 mg (0.32 mmol) 7,7-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine hydrochloride and 0.12 mL TEA in 1.0 mL DMF and the mixture was stirred for 4 h 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-95b2ee37269049ffacae9cebd6909a49
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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