O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 58386737, compound

HRID 74698Notes

Reaction equation

HRID 74698 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]=[C:17]([C:21](O)=[O:22])[CH:16]=3)[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:24]=[CH:25][CH:26]=[CH:27][C:4]=2[NH:3]1.[NH:28]1[C:38]2[C:39]3[CH:30]([CH2:31][C:32](=[O:40])[NH:33][C:34]=3[CH:35]=[CH:36][CH:37]=2)[CH2:29]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[O:1]=[C:2]1[NH:3][C:4]2[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=2[CH2:6][CH2:7][N:8]1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][N:18]=[C:17]([C:21]([N:28]3[C:38]4[C:39]5[CH:30]([CH2:31][C:32](=[O:40])[NH:33][C:34]=5[CH:35]=[CH:36][CH:37]=4)[CH2:29]3)=[O:22])[CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 104421921,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-oneHCID 583864046-[4-(2-Oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid

Product 1

HCID 58386737HCID 58386737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

63mg (0.17 mmol) 6-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid and 30 mg (0.17 mmol) 1,2,2a,5-tetrahydro-3H-pyrrolo-[4,3,2-de]quinolin-4-one in 56 μL (0.40 mmol) TEA and 1.8 mL DMF were mixed with 58 mg (0.18 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-e3864c8e1a2644cf9abd6589fdc61f5f
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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