1-Hydroxybenzotriazole → HCID 23598696, compound

HRID 891198Notes

Reaction equation

HRID 891198 reaction equation
C(O[C:5](=[O:16])[NH:6][C:7]1[CH:8]([O:13][CH2:14][CH3:15])[O:9][C:10](=[O:12])[CH:11]=1)C=C.C([SiH2][O:22][C:23](C)(C)[C:24]1[CH2:30][N:29]([CH2:31]C(O)=O)[C:28](=[O:35])[CH:27]([NH:36][C:37]([C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=[CH:41][N:40]=2)=[O:38])[CH2:26][CH:25]=1)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.C(Cl)Cl.CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:22][CH2:23][C:24]1[CH2:30][N:29]([CH2:31][C:5](=[O:16])[NH:6][CH:7]2[CH2:11][C:10](=[O:12])[O:9][CH:8]2[O:13][CH2:14][CH3:15])[C:28](=[O:35])[CH:27]([NH:36][C:37]([C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=[CH:41][N:40]=2)=[O:38])[CH2:26][CH:25]=1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69601293HCID 69601293, compoundHCID 131725291HCID 131725291, compound

Product 1

HCID 23598696HCID 23598696, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A catalytic amount of Pd(Ph3P)4 is added to a solution of (2-Ethoxy-5-oxo-furan-3-yl)-carbamic acid allyl ester (0.24 g, 1.0 mmol) and N,N-dimethylbarbituric acid (0.38 g, 2.4 mmol) in CH2Cl2 (5 mL). The solution is stirred for 15 minutes at room temperature after which {6-(tert-butyl-dimethyl-silanyloxymethyl)-3-[(isoquinoline-1-carbonyl)amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid, 22, (0.15 g) is added as a solution in CH2Cl2/DMF (2 mL, 1:1), followed by HOBt (0.126 g, 0.93 mmol) and EDCl (0.18 g, 0.93 mmol). The solution is stirred for 5 hours, diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (Na2SO4), and concentrated in vacuo. The resulting residue us purified over silica (EtOAc/hexane) to afford the desired compound.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue us purified over silica (EtOAc/hexane)

Sources & evidence

ORD record
ord-8ed1daf36ae944d7817a0b4b248953e2
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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