1-Hydroxybenzotriazole → HCID 23598704, compound

HRID 891207Notes

Reaction equation

HRID 891207 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:17]([NH:25][CH2:26][C:27]1[CH2:33][N:32]([CH2:34]C(O)=O)[C:31](=[O:38])[CH:30]([NH:39][C:40]([C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=[CH:44][N:43]=2)=[O:41])[CH2:29][CH:28]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.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>[C:17]([NH:25][CH2:26][C:27]1[CH2:33][N:32]([CH2:34][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:31](=[O:38])[CH:30]([NH:39][C:40]([C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=[CH:44][N:43]=2)=[O:41])[CH2:29][CH:28]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22243177HCID 22243177, compoundHCID 69601293HCID 69601293, compound

Product 1

HCID 23598704HCID 23598704, 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 (100 mg, 0.43 mmol) and N,N-dimethylbarbituric acid (135 mg, 0.86 mmol) in CH2Cl2 (5 mL). The solution is stirred at room temperature for 15 minutes then {6-(benzoylamino-methyl)-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid, 31, prepared in the previous step, is dissolved in CH2Cl2/DMF (2 mL of 1:1) and added. HOBt (54 mg, 0.40 mmol) and EDCl (77 mg, 0.40 mmol) are added and the solution stirred for 5 hours after which time it is diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (Na2SO4), and concentrated in vacuo. The resulting residue is purified over silica (EtOAc/hexane) to afford the desired product.

Workup

  1. additionadded
  2. stirringthe solution stirred for 5 hours after which time it
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified over silica (EtOAc/hexane)

Sources & evidence

ORD record
ord-3bf8cb90fa4c4c1fbd5c6b8320a83abe
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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