Hydrochloric Acid → HCID 67317217, compound

HRID 1012989Notes

Reaction equation

HRID 1012989 reaction equation
C([N:8]([CH3:33])[CH:9]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][N:11]2[C:23](=[O:32])[C:24]([OH:31])=[C:25]([C:27](OC)=[O:28])[N:26]=[C:10]12)C1C=CC=CC=1.Cl.[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][C:37]=1[CH3:44]>CO.[Pd]>[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:27]([C:25]2[N:26]=[C:10]3[CH:9]([NH:8][CH3:33])[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:13][CH2:12][N:11]3[C:23](=[O:32])[C:24]=2[OH:31])=[O:28])=[CH:38][C:37]=1[CH3:44]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2774599(4-Fluoro-3-methylphenyl)methanamineHCID 673173728-tert-butyl 2-methyl 10-[benzyl(methyl)amino]-3-hydroxy-4-oxo-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-2,8(4H)-dicarboxylate

Product 1

HCID 67317217HCID 67317217, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-tert-butyl 2-methyl 10-[benzyl(methyl)amino]-3-hydroxy-4-oxo-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-2,8(4H)-dicarboxylate prepared as described in Step 4, was dissolved in MeOH, treated with 1 N HCl (1 eq.) and stirred overnight under an H2 atmosphere in the presence of 10% Pd/C. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure. MS (ES) C16H24N4O6 requires 368. Found: 369 (M+H+). The crude organic product was taken in methanol and treated with 1.2 eq. of 4-fluoro-3-methyl-benzylamine and resulting mixture was refluxed overnight. After cooling to room temperature, evaporation of volatiles under reduced pressure yielded title product which was directly taken in the next step. MS (ES) C23H30FN5O5 requires 475. Found: 476 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customresulting mixture
  4. temperaturewas refluxed overnight
  5. customevaporation of volatiles under reduced pressure

Sources & evidence

ORD record
ord-9715206ae3034db28bf54d1255583807
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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