Diisopropylethylamine → (+/-)-2-[2-[[4-[5-(7-Ethyl-2-methyl-4H-benzo[5,6]cyclohept[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]pyrimidin-2-yl]amino]acetylamino]-4-thiazoleacetic acid, ethyl ester

HRID 324403Notes

Reaction equation

HRID 324403 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]=[C:12]([CH:14]3[C:20]4[N:21]=[C:22]([CH3:24])[O:23][C:19]=4[CH:18]=[CH:17][C:16]4[CH:25]=[C:26]([CH2:29][CH3:30])[CH:27]=[CH:28][C:15]3=4)[C:11](=[O:31])[NH:10][C:9]2=[O:32])[CH:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:42]([O:44][C:45](=[O:57])[CH2:46][C:47]1[N:48]=[C:49]([NH:52][C:53](=[O:56])[CH2:54][NH2:55])[S:50][CH:51]=1)[CH3:43]>CN1CCCC1=O>[CH2:29]([C:26]1[CH:27]=[CH:28][C:15]2[CH:14]([C:12]3[C:11](=[O:31])[NH:10][C:9](=[O:32])[N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:55][CH2:54][C:53]([NH:52][C:49]5[S:50][CH:51]=[C:47]([CH2:46][C:45]([O:44][CH2:42][CH3:43])=[O:57])[N:48]=5)=[O:56])[N:7]=4)[CH:13]=3)[C:20]3[N:21]=[C:22]([CH3:24])[O:23][C:19]=3[CH:18]=[CH:17][C:16]=2[CH:25]=1)[CH3:30]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 54551034Ethyl 2-(2-(2-aminoacetamido)thiazol-4-yl)acetateHCID 88152174(+/-)-1-(2-Chloropyrimidin-4-yl)-5-(7-ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 131722503(+/-)-2-[2-[[4-[5-(7-Ethyl-2-methyl-4H-benzo[5,6]cyclohept[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]pyrimidin-2-yl]amino]acetylamino]-4-thiazoleacetic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the products from steps (viii) (0.65 g) and (ix) (1.025 g) and N,N-diisopropylethylamine (1.26 ml) in N-methylpyrrolidin-2-one (10 ml) was stirred at 90° C. for 24 hours. A further 0.342 g of product from step (ix) and N,N-diisopropylethylamine (0.5 ml) was added and heating continued for a further 24 hours. The solution was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was washed with water, dried (MgSO4) and evaporated to give a brown oil which was purified by chromatography eluting with ethyl acetate.

Workup

  1. temperatureheating
  2. waitcontinued for a further 24 hours
  3. customThe solution was partitioned between 1N hydrochloric acid and ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a brown oil which
  8. customwas purified by chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0009afbe1b7e40a7879fbe983f6a5173
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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