Triethylamine → 2-(3-{2-amino-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-pyrimidin-4-yl}propyl)isoindole-1,3-dione

HRID 1035478Notes

Reaction equation

HRID 1035478 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23](=O)[C:24]#[C:25][CH2:26][CH2:27][CH2:28][N:29]4[C:37](=[O:38])[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:30]4=[O:39])=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:11]=[N:10]1.C(=O)(O)O.[NH2:45][C:46]([NH2:48])=[NH:47]>COCCO>[NH2:48][C:46]1[N:47]=[C:25]([CH2:26][CH2:27][CH2:28][N:29]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:39])[CH:24]=[C:23]([C:22]2[C:16]3[C:17](=[N:18][CH:19]=[C:14]([C:12]4[CH:11]=[N:10][N:9]([CH3:8])[CH:13]=4)[CH:15]=3)[NH:20][CH:21]=2)[N:45]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 286947Carbonic acid-guanidine (1:1)HCID 582170912-{6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-6-oxohex-4-ynyl}isoindole-1,3-dione

Product 1

HCID 582170902-(3-{2-amino-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-pyrimidin-4-yl}propyl)isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

8.5 0.92 ml (6.7 mmol) of triethylamine is added to a solution of 116 mg (0.265 mmol) of 2-{6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-6-oxohex-4-ynyl}isoindole-1,3-dione and 70 mg (0.39 mmol) of guanidine carbonate in 4 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 6 hours. After cooling, the mixture is evaporated, and the residue is purified by preparative HPLC, giving 2-(3-{2-amino-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-pyrimidin-4-yl}propyl)isoindole-1,3-dione as brown solid; ESI 479, EMD 1183586.

Workup

  1. temperaturethe mixture is heated at the boil for 6 hours
  2. temperatureAfter cooling
  3. customthe mixture is evaporated
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-35cef5fe2ded444892205d1a5a3d5315
Source dataset
uspto-grants-2013_10
Patent number
US08546390B2

Reaction notes

Loading…