Triethylamine → HCID 66923969, compound

HRID 1360199Notes

Reaction equation

HRID 1360199 reaction equation
[C:1]12([NH:11][C:12]3[C:17](C(O)=O)=[CH:16][N:15]=[C:14]4[NH:21][CH:22]=[CH:23][C:13]=34)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([N:26](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:48]1[CH2:53]COCC1>>[C:1]12([N:11]3[C:12]4=[C:13]5[CH:23]=[CH:22][NH:21][C:14]5=[N:15][CH:16]=[C:17]4[NH:26][C:53]3=[O:48])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 199401P,P-Diphenylphosphinic azideHCID 57928615HCID 57928615, compound

Product 1

HCID 66923969HCID 66923969, compound

Procedure

4-(Adamantan-1-ylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (17 mg) and triethylamine (15 μl) were dissolved in dioxane (0.5 ml). To the mixture was added diphenylphosphoryl azide (DPPA) (18 μl) at 120° C. under stirring. The mixture was stirred at the same temperature for 2 hours and cooled to ambient temperature. The obtained solid was collected by filtration and washed with acetonitrile to obtain (adamantan-1-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one (11 mg).

Workup

  1. stirringThe mixture was stirred at the same temperature for 2 hours
  2. filtrationThe obtained solid was collected by filtration
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-5d5bf4a720ed45cd97a8f847cacbfc94
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

Loading…