Triethylamine → HCID 22649315, compound

HRID 393237Notes

Reaction equation

HRID 393237 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.Cl.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:27][C:28](=[O:44])[NH:29][C:30]1[C:31]2[S:38][C:37](/[CH:39]=[CH:40]/[C:41]([OH:43])=O)=[CH:36][C:32]=2[N:33]=[CH:34][N:35]=1.[N:45]1([CH2:51][CH2:52][NH2:53])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.C(N(CC)CC)C>CN(C=O)C>[Cl:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[C:21]=1[NH:27][C:28](=[O:44])[NH:29][C:30]1[C:31]2[S:38][C:37](/[CH:39]=[CH:40]/[C:41]([NH:53][CH2:52][CH2:51][N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[O:43])=[CH:36][C:32]=2[N:33]=[CH:34][N:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33944N-(2-Aminoethyl)piperidineHCID 199401P,P-Diphenylphosphinic azideHCID 69041510HCID 69041510, compound

Product 1

HCID 22649315HCID 22649315, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diphenylphosphoryl azide (0.085 ml) was added to a mixture of (E)-3-{4-[3-(2,6-dichlorophenyl)ureido]thieno[3,2-d]pyrimidin-6-yl)acrylic acid hydrochloride salt (0.11 g), 2-piperidinoethylamine (0.064 g), triethylamine (0.07 ml) and DMF (1.5 ml). The mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was triturated under diethyl ether, isolated, washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.087 g); NMR Spectrum: (DMSOd6 and CF3COOD) 1.3-1.5 (m, 1H), 1.6-1.8 (m, 4H), 1.85 (d, 2H), 2.95 (t, 2H), 3.2 (t, 2H), 3.55 (d, 2H), 3.6 (t, 2H), 6.82 (d, 1H, J=16 Hz), 7.4 (t, 1H), 7.6 (d, 1H), 7.86 (s, 1H), 7.86 (d, 1H), 8.95 (s, 1H); Mass Spectrum: M+H+ 519 and 521.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  4. customThe material so obtained
  5. customwas triturated under diethyl ether
  6. customisolated
  7. washwashed with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3c8d5641276f46f7b3ea68e2f30416dc
Source dataset
uspto-grants-2004_10
Patent number
US06806274B1

Reaction notes

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