1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

HRID 2376004Notes

Reaction equation

HRID 2376004 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:36]=[CH:35][C:16]([C:17]([N:19]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]3[S:26][CH:27]=[C:28](/[CH:30]=[CH:31]/[C:32](O)=[O:33])[N:29]=3)[CH2:20]2)=[O:18])=[CH:15][CH:14]=1.[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:43][NH2:44].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.CCOC(C)=O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([N:19]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]3[S:26][CH:27]=[C:28](/[CH:30]=[CH:31]/[C:32]([NH:44][O:43][CH:38]4[CH2:39][CH2:40][CH2:41][CH2:42][O:37]4)=[O:33])[N:29]=3)[CH2:20]2)=[O:18])=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 86603626(2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)acrylic acid

Product 1

HCID 86603627(2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamideYield 87.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDCI (0.30 g) was added to the solution of (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)acrylic-acid (0.6 g), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (0.22 g), and HOBT (0.26 g) in DMF (10 ml) under ice-cooling and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was poured into a mixture of AcOEt and water. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (0.66 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ebc754e70d5d467fa5957404ce918a5d
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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