1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → CID 145857197

HRID 10987

Reaction equation

HRID 10987 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1)[C:12]1[C:17](=[O:18])[N:16]2[C@H:19]([C:22](O)=[O:23])[CH2:20][CH2:21][C:15]2=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]([O:40][C:41](=[O:53])[NH:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([CH2:51][NH2:52])=[CH:47][CH:46]=1)=[NH:44])([CH3:39])([CH3:38])[CH3:37].C([O-])(O)=O.[Na+].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CCOC(C)=O.C(Cl)Cl.CN(C=O)C>[C:36]([O:40][C:41]([NH:42][C:43](=[NH:44])[C:45]1[CH:46]=[CH:47][C:48]([CH2:51][NH:52][C:22]([C@H:19]2[N:16]3[C:17](=[O:18])[C:12]([N:11]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=4)[C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:13][N:14]=[C:15]3[CH2:21][CH2:20]2)=[O:23])=[CH:49][CH:50]=1)=[O:53])([CH3:39])([CH3:37])[CH3:38]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 57444827(S)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic AcidHCID 145832046tert-butyl N-[4-(aminomethyl)benzenecarboximidoyl]carbamate

Product 1

HCID 145857197CID 145857197Yield 79.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of intermediate 25a (0.281 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester (84 mg, 0.337 mmol) in 3 mL 5:1 CH2Cl2/DMF at 0° C., were added NaHCO3 (59 mg, 0.703 mmol), HOAT (42.1 mg, 0.309 mmol), and EDCI (75.5 mg, 0.393 mmol). The mixture was allowed to warm to rt and stir 20 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, and sat. NaHCO3, and brine, dried (Na2SO4) and brine. The crude residue was triturated with Et2O to afford 160 mg (79%) of intermediate 25b as a white solid. MS (ESI) 719.4 (M+H+).

Workup

  1. washThe organic phase was washed with H2O, 1N HCl, H2O, and sat. NaHCO3, and brine
  2. dry with materialdried (Na2SO4) and brine
  3. customThe crude residue was triturated with Et2O

Sources & evidence

ORD record
ord-f36da15899fd4af9811f6c580396af9c
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Linked notes

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