Tris(hydroxymethyl)aminomethane → HCID 67278468, compound

HRID 1696265Notes

Reaction equation

HRID 1696265 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][NH:16][C:13]4=[N:14][CH:15]=[C:10]3[NH:9][C:8]2=[O:19])[CH2:2]1.ON1C2C=CC=CC=2N=N1.[C:30](O)(=[O:34])[CH2:31][CH:32]=[CH2:33].N=C=N.C(O)C(N)(CO)CO.[N-]=C=O>>[C:30]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][NH:16][C:13]4=[N:14][CH:15]=[C:10]3[NH:9][C:8]2=[O:19])[CH2:2]1)(=[O:34])[CH2:31][CH:32]=[CH2:33]

Participants

7

Reactant 6

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 327433-Butenoic acidHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435CarbodiimideHCID 67278038HCID 67278038, compound

Product 1

HCID 67278468HCID 67278468, compound

Procedure

A mixture of 1-piperidin-3-yl-3,6-dihydroimidazo[4,5-d]-pyrrolo[2,3-b]pyridin-2(1H)-one (0.030M solution in N,N-dimethylformamide, 1.00 mL), 1-hydroxybenzotriazole (4.1 mg, 0.030 mmol), 3-but-enoic acid (0.50M solution in NMP, 0.080 mL), and PS-Carbodiimide (Argonaut technologies,50 mg) was agitated at ambient temperature for 16 hours. PS-Trisamine (Argonaut technologies, 50 mg), PS-Isocyanate (50 mg) was added and the reaction agitated at ambient temperature for a further 2 hours and filtered. The filtrate was concentrated to yield 1-(1-but-3-enoylpiperidin-3-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (9.7 mg).

Workup

  1. stirringthe reaction agitated at ambient temperature for a further 2 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7d68168ff83c4bde8024b447bbe6e53e
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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