Triethylamine → HCID 58386428, compound

HRID 74638Notes

Reaction equation

HRID 74638 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[CH:21][N:20]=[C:19]([C:23](O)=[O:24])[CH:18]=2)[CH2:13][CH2:12]1.[N:26]1([CH2:31][CH2:32][CH2:33][CH:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:36][CH2:35]2)[CH2:30][CH2:29][CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[N:26]1([CH2:31][CH2:32][CH2:33][CH:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([C:23]([C:19]3[N:20]=[CH:21][N:22]=[C:17]([N:14]4[CH2:13][CH2:12][CH:11]([N:3]5[C:4]6[C:5](=[N:6][CH:7]=[CH:8][CH:9]=6)[NH:10][C:2]5=[O:1])[CH2:16][CH2:15]4)[CH:18]=3)=[O:24])[CH2:35]2)[CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58386466HCID 58386466, compoundHCID 583866966-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 58386428HCID 58386428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

140 mg (0.41 mmol) 6-[4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 94.4 mg (0.41 mmol) 3-(3-pyrrolidin-1-yl-propyl)-2,3-dihydro-1H-indole, 138.2 mg (0.43 mmol) TBTU and 112 μL (0.8 mmol) triethylamine in 4 mL DMF were stirred overnight at RT. The mixture was separated by preparative HPLC. The product fractions were combined and lyophilised.

Workup

  1. customThe mixture was separated by preparative HPLC

Sources & evidence

ORD record
ord-cea831bc80c34498b6a690c29584f032
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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