Triethylamine → HCID 42613374, compound

HRID 74640Notes

Reaction equation

HRID 74640 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]([OH:25])=O)[CH:18]=2)[CH2:13][CH2:12]1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2([CH2:37][CH2:36][CH2:35]2)[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([C:23]([C:19]2[N:20]=[CH:21][N:22]=[C:17]([N:14]3[CH2:13][CH2:12][CH:11]([N:3]4[C:4]5[C:5](=[N:6][CH:7]=[CH:8][CH:9]=5)[NH:10][C:2]4=[O:1])[CH2:16][CH2:15]3)[CH:18]=2)=[O:25])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2([CH2:37][CH2:36][CH2:35]2)[CH2:27]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27274706Spiro[cyclobutane-1,3'-indoline]HCID 583866966-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 42613374HCID 42613374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

214 mg (0.63 mmol) 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 100 mg (0.628 mmol) spiro[cyclobutane-1,3′-indoline], 212 mg (0.66 mmol) TBTU and 168 μL (1.20 mmol) triethylamine in 4 mL DMF were stirred overnight at RT. The mixture was separated by preparative HPLC. The product fractions were combined and the acetonitrile was removed using the rotary evaporator. The precipitated substance was suction filtered, washed with 20 mL water and dried in the CAD at 50° C.

Workup

  1. customThe mixture was separated by preparative HPLC
  2. customthe acetonitrile was removed
  3. customthe rotary evaporator
  4. filtrationfiltered
  5. washwashed with 20 mL water
  6. customdried in the CAD at 50° C.

Sources & evidence

ORD record
ord-28b59d7e43784e6abb19fcde61e2c949
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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