Acetic Acid → HCID 22632619, compound

HRID 2417498Notes

Reaction equation

HRID 2417498 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:52]=[CH:51][C:12]([C:13]([N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][C:24]([CH2:26][CH2:27][C:28](=[O:35])[N:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[CH:25][C:19]=3[N:18]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([N:45]4[CH2:49][CH:48]=[CH:47][CH2:46]4)=[O:44])=[CH:39][CH:38]=3)[C:17](=[O:50])[CH2:16]2)=[O:14])=[CH:11][CH:10]=1.C=O.[C:55](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][C:24]([CH2:26][CH2:27][C:28]([N:29]4[CH2:34][CH2:33][N:32]([CH3:55])[CH2:31][CH2:30]4)=[O:35])=[CH:25][C:19]=3[N:18]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([N:45]4[CH2:46][CH:47]=[CH:48][CH2:49]4)=[O:44])=[CH:39][CH:38]=3)[C:17](=[O:50])[CH2:16]2)=[O:14])=[CH:51][CH:52]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22632657HCID 22632657, compound

Product 1

HCID 22632619HCID 22632619, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (0.014 mmol) of 4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-8-[3-oxo-3-(1-piperazinyl)propyl]-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on trifluoroacetate was dissolved in 2 ml of dichloromethane. 5 mg of paraformaldehyde and 0.005 ml (0.09 mmol) of acetic acid were added to the obtained solution and they were stirred at room temperature for 30 minutes. 24 mg (0.12 mmol) of sodium triacetoxyborohydride was added to the obtained mixture and they were stirred at room temperature overnight. The solvent was evaporated and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. stirringwere stirred at room temperature overnight
  2. customThe solvent was evaporated
  3. customthe obtained crude product
  4. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-c829aeacf291403c83ee915ed3260fd0
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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